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Posts Tagged ‘genitalia’

Take It Easy

I’m dating a Catholic virgin (both of us are professional adults).  We’re going to have sex soon, and I want to make it good for her, but I’m not very experienced myself and I’m both long and thick; I have to buy custom condoms because nothing store-bought fits.  Worse, I have a pronounced downward bend; it caused problems with my first-ever girlfriend, and that left a lasting impression on me.  I really don’t want to ruin this for her; do you have any advice?

The most important advice I can give you about this is, DON’T RUSH.  If she’s a virgin your size may scare her at first, so you need to be ready for that possibility.  If it happens, you need to sincerely tell her that it’s not a rush, and you have to mean it so she sees it in your eyes and believes you.  Start with fingers and oral, to get her ready before you even try; if she has an aversion to fingers, try gently explaining that you’re concerned about hurting her so you want to take it slow & get her ready.  The vagina can take a LOT more than any human man has; lesbians often fist each other (which even though women’s hands are smaller than men’s, are still MUCH thicker than penises).  Plus, babies, right?  But that’s after warmup and relaxation.  So anything you can do to help her relax is a bonus; a few cocktails (you don’t want her drunk, just relaxed) or some good cannabis are time-tested methods.  When you do start the actual penetration process, don’t be in a rush; a little at a time, with kissing and touching, will help her to stay calm and relaxed.  And make sure you have plenty of water-based lube on hand; women vary in the amount they lubricate naturally, and if she’s nervous she may be drier than under optimal conditions.  Plus, condoms require more lube than bareback sex; the latex produces more friction than bare skin.  If she does get scared and changes her mind, don’t get angry; that isn’t uncommon.  Just gently withdraw and assure her that it’s OK, and that y’all can try again another time (again, you need to mean it because she’ll know if you’re just saying it).

Just because she’s a virgin does not mean she’ll be super-tight; women’s genitalia come in all sizes just as men’s do, so once she gets over the nervousness you may fit quite well.  And it’s a myth that a lot of sex loosens a woman; after 36 years of sex I’m still extremely tight.  What some guys mistake for loosening is just the woman learning to relax, which of course increases with experience (childbirth can also damage the muscles, but that’s a subject for another day).  It’s possible that your angle may cause an issue, especially if it’s pronounced; you may need to try a couple of different positions to see which one works best for her.  Reverse cowgirl (woman on top, facing the man’s feet) can be good for penises with a pronounced downward bend, and that has the bonus of letting her control the rate and depth; of course, that also results in deper penetration, which is not so good for a long cock.  So you’ll probably need to experiment to see what’s best.  Incidentally, I believe there has been some progress in the treatment of Peyronie’s Syndrome (that’s what the pronounced bend is called), so you may want to talk to your doctor for referral to a specialist for consultation.

Finally, and VERY importantly, do not worry about your skill level.  Really, honestly, that is of little to no consequence to most women.  What’s important is that you be loving, gentle and patient; that you listen to what she says and watch her nonverbal cues about what feels good and what doesn’t; that you make her feel beautiful, desirable and loved, and not pressured or inadequate; and that you help her understand that more than anything else you want intimacy with her, specifically, and not just any attractive woman.  And that because of that last, you’re willing to take your time and do whatever it takes to make her happy and comfortable.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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I’m over 70 and no longer able to get an erection even with the meds available.  I’m in good shape, not bad looking and can afford it, but am reluctant to engage a girl.  What do you think?

One thing that I (and nearly nearly every sex worker I talk to) wish men understood is that we really don’t care about most of the things men think women care about, and that includes most of the things some amateur women do care about.  We really don’t care about clients’ looks, age, relative levels of physical fitness, penis size, ability to perform tricks they saw in porn movies or anything like that; what we do care about is that our clients are polite, generous, clean, respectful, prompt, appreciative, gentlemanly and realistic about their expectations.  What I mean by that last is, it’s not a problem if a gentleman is unable to get an erection, understands that, and asks for activities that don’t require one (of which there are many); the problem only arises (no pun intended) if he believes a whore can perform the sexual equivalent of a resurrection, and gets angry at her if she can’t.  In my career I’ve had plenty of men, including many younger than yourself, who were suffering from temporary or permanent erectile dysfunction, and as long as they understood and accepted that we were still able to have a good time cuddling, kissing, playing with toys, engaging in kink and other such activities that don’t involve erections.  But when such a man expected some kind of high-level sexual witchcraft beyond even my considerable skills, it rarely turned out well.  My advice to you, then, is to find a mature lady whose company you think you’ll enjoy regardless of what happens in the bedroom; go into the date knowing your limitations and clearly communicate those limitations to her; and enjoy the journey rather than being hell-bent on reaching some kind of destination to which there may no longer exist a bridge.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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Regular readers know that I’m not usually one for giving testimonials, and never unless I actually try and like a product.  And that doesn’t happen all that often for the simple reason that I’m rather set in my ways, so it isn’t often I actually try a new product to discover whether I like it or not.  But when the product A) was developed by a very dear friend; B) is derived from cannabis; and C) is intended to intensify orgasms…well, obviously I was much more motivated than usual to try it.  The product, as most of you can probably guess, is Mistress Matisse’s new Velvet Swing, a cannabis-infused lube which enhanced orgasm in 80% of the women who tried it during the testing phase; I bought some at the official product launch three weeks ago, but it took until last week to try it because I really wanted to give it a fair test.

Many of you may recall that I don’t orgasm easily or often; I have a recessed clitoris (which makes external stimulation generally ineffective), plus most people aren’t willing or able to give me the kind of stimulation I need for long enough and hard enough to actually get me where I need to go.  And to make things worse, it’s extremely difficult to get my overactive brain to relax enough for me to actually achieve the proper headspace unless one or more of my kinks are engaged intensely enough to nullify my high distractibility.  So needless to say, I wasn’t sanguine about the possibility of any lube, cannabis-infused or otherwise, doing much for me; I’m used to being a statistical outlier in anything to do with sex, so I figured it was very likely I’d be in that 20% the product didn’t do much for.  On the other hand, cannabis tends to have very strong effects on me; 20 or 25 mg of edible and I’m good for the whole evening, and my trips are very intense and border on the psychedelic, including full audiovisual effects (visions and hallucinations).  So if any sexual product could enhance my orgasms, a cannabis-based product would probably have the best chance.  Given all those facts, I figured it was best I try the product with someone I’ve been with often, and whose primary interaction with me is vanilla instead of kink (so that I’d be able focus on what was happening in my genital region rather than on my endorphin high).  On the 31st I spent the night with one of my favorite regulars, and I knew he wouldn’t mind (because SCIENCE!)

I used 10 pumps, the maximum regular dose, because I didn’t want there to be any doubt in my mind; I rubbed it onto my clitoris, between my labia and into my vagina, and then we kept ourselves occupied for 40 minutes to allow it to achieve maximum effect (as recommended).  By the 30-minute mark I experienced a distinct tingling, and when he started to touch me I found the sensation much more intense than it would normally be; he was able to give me six orgasms with manual stimulation alone, a feat which nobody (male or female) has ever achieved before.  The first orgasm was a fairly big one and the other five were just little ones, but given that external stimulation doesn’t normally result in any orgasms, big or small, that’s pretty damned impressive.  I didn’t really notice a lot of difference in the stimulation resulting from penetration, though my labia & vagina did seem “fuller”, more engorged.  As the old commercials used to say, Your Mileage May Vary; however, if you live in or can travel to Seattle (it’s not sold anywhere else yet), I’d definitely recommend trying it.  I plan to again at the next available opportunity; next time with a woman, I think!

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It happened again this week:  somebody emailed me a question that I could answer, but won’t.

When I first started this blog seven years ago, I was just a little past 40 and still a little bit naive about the capacity of humans to handle unpleasant truths.  Of course I recognized that most people prefer to live in blissful ignorance than to have their comfortable delusions challenged, but I foolishly believed that the sort of person who would read a blog specifically offering “frank commentary” from a hooker would be different.  And you know what?  I was wrong.  Just because someone’s against the establishment and wants to change the status quo doesn’t make them open-minded; very often, it just means they want to establish their own censorious, oppressive status quo.  So during the first year I was writing The Honest Courtesan, I often stepped on the toes of people who weren’t actually my enemies, and against whom I meant no disrespect or offense.  Sometimes it was because I was wrong; sometimes it was because I was basically right, but expressed myself in a clumsy or offensive way; and sometimes it was because I was completely right, but the objectors simply didn’t like what I was saying so they mischaracterized it as something else or simply denied that I was qualified to opine on the subject at all.  The majority of the times the latter happened, it was because I’m not a member of whatever group the question involved; on a few occasions, people who wanted to be offended have actually claimed I wasn’t a member of some group that I actually am a member of, so as to have an excuse to attack me.  I’ve had women claim I was never raped because they were angry that I challenge neofeminist bullshit about rape; before I went back to work prohibitionists would often claim I had never been a whore (it’s kinda hard to do that now that my escort ads are easily found on Google by typing in “Maggie McNeill Seattle escort”); and before I was showing my face in copious selfies and freaking TELEVISION APPEARANCES, some idiots who thought themselves clever tried to claim I was a man (specifically a client) because they didn’t want to believe that a woman might not think like them.

At first, this didn’t really bother me, but now I’m over 50 and operating in a chronic state of emotional exhaustion, and people with axes to grind are just looking for excuses to undermine my work by making asinine accusations against me; some of these are even sex workers for whom ideological purity trumps actually unifying to fight for decriminalization.  So I’m sorry, but I will no longer answer controversial questions about groups that I’m not a member of.  If your question is about women in general, or sex workers, or bisexual women, or kinky people, or any other group I’m part of, fire away and it can be as controversial as you like.  And if your question involves some group of which I’m not a member such as nonwhite people, trans people, heterosexual people or whatever and it isn’t controversial, fire away and I’ll answer as best I can.  But if you have some question which arouses considerable acrimony and involves a group I’m not part of?  Forget it.  I’ve been directly told, for example, that I’m not allowed to have an opinion on circumcision because I don’t have a penis, even if that opinion is based in data from published studies.  And while I think that’s nonsense, I’m too tired to fight it any more; you’ll need to address such questions to a member of whatever group is allowed to have opinions on the subject.  Sorry about that; I’m not masochistic enough to enjoy beating my head against a brick wall.

The one exception is questions about those in power, of course; I’ve never held political power, but I’ll opine on those sociopaths all day long.  Fuck them.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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Prolong

I would like to be able to “hold” longer; I am not a premature ejaculator, but I’d definitely would love to have the whole exercise last longer.  I am always amazed when watching porn film clips, to see these actors last so long, even with hearty stimulation going on.  What is their secret recipe?  Are there any pills/medications that would help?

I have a simple question: Why?  For what reason do you want to last longer?  A lot of men seem to think sex is some kind of endurance contest, and the longer they can go without orgasm, the better.  To be sure, cultural messaging is part of that; the media can’t handle subtlety, and so “not instantly” is transmogrified into “going on and on and on for half a bloody hour”, when in actuality most women don’t want the act of intercourse to last more than five or ten minutes.  Of course there are exceptions; some gals just adore being pistoned into for 20 minutes or more,  but I can assure you that they are in the minority.  When women say they want sex to take a long time, they don’t mean they want intercourse to be some kind of porn marathon; they mean they want the whole process, from the initial hand-holding and kissing until the final parting or sleeping after cuddling, to be unhurried and natural.  The actual pumping is only a small part of that.

As for porn, please remember that it’s no more realistic than any other form of video entertainment.  In real life, people don’t generally fall in love within two hours and live happily ever after; problems aren’t neatly tied up in time for the end credits; doctors and cops don’t have exciting, important cases every week; and the heroes & villains aren’t totally distinct and distinguishable by the color of their hats.  Porn actors’ most important talent is being able to perform under the weird conditions required for the filming of porn, which are anything but sexy; however, you also have to remember that porn (like any other movie) isn’t filmed in one real-time take.  There’s a lot of stopping, starting, redoing, multiple takes, editing, cutting, etc; the scenes may not even have been filmed in the order you see them.  Just because it looks to you that Dick Dongmeister fucked for 40 minutes straight doesn’t mean it actually happened that way, and just because the actress seemed to like being fucked for that long doesn’t mean she actually did (or that she actually was).  It’s called “acting” for a reason.  Furthermore, in real life, very few women can get off from just penetration; they generally want more clitoral stimulation than pounding.  So if the actual endurance is for some reason important to you, there are numbing creams and sprays (containing a topical anesthetic, same as in toothache remedies) available at adult stores (or, according to Google, regular pharmacies) that may do the trick.  But if the reason you want to last longer is to increase your partner’s pleasure, you’d be much better off just learning to ask her what she wants and giving her more of whatever that is.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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I’m a 27 year old virgin who was raised in a Puritanical family to believe that Sex was dirty, evil and wrong; I masturbated when alone, watched porn when I could, but never tried to touch a woman for real because I believed that there was some pure virgin woman out there, waiting for someone exactly like me who, when we got married, would satisfy every sexual desire I had.  But when I got to college I started to realize that both good girls AND bad girls have sex, and the mysterious, untouched, pristine virginal woman who would wait for years until marriage to have sex, basically didn’t exist.  I’ve tried dating, but every woman seemed to view me as “friend zone” material until I recently found one on an online dating app who is perfect in every possible way.  In two months of online interaction I’ve fallen head over heels for her, and next month I’ll be flying to her state to meet her in person and spend a week with her.  However, she is not a virgin; in fact, she’s quite experienced and can’t wait to “have all kinds of naughty fun” with me.  But I haven’t the slightest idea of how to please her!  I told her I was a virgin, and she told me that’s okay.  But, I don’t know how to do cunnilingus, I don’t know how to move from one activity to another, and I’m not sure if my penis is big enough to satisfy her.  And my fear is, I will lose her if I don’t satisfy her on this trip.  What should I do?  Should I visit an escort so I can practice?  Any advice you can give me is greatly appreciated!

shy guyThis might seem weird coming from me, but DO NOT see a sex worker or otherwise make any attempt to lose your virginity before meeting up with your lady.  You told her you’re a virgin, and she said that’s OK; it’s entirely possible that it’s even more than OK, and in fact may be something she specifically finds desirable in you.  Some women like breaking virgins in; sometimes it’s a turn-on in and of itself, and sometimes it may be that they enjoy “training” a guy to do things the way they want them done.  Now, it may be that your lady isn’t specifically interested in your virginity, and that she doesn’t care one way or the other.  But it’s also possible she might feel kind of cheated if she was looking forward to that and you went and screwed it up without good reason on the eve of your meeting.  Note:  I am not saying that anyone “owes” a new partner virginity, or that sexual experience is a bad thing (and I am not going to be a pot describing the color of kettles).  All I’m saying is that I see no valid reason for you to make a liar out of yourself when you may be fulfilling a fantasy of hers (which I think you’ll agree would be pretty awesome).

Don’t worry about not knowing what to do; trust me, she already expects that.  Lots of men who think they know what they’re doing in bed actually don’t know shit, and since she’s quite experienced I’m sure she’s been with more than a few of those (incredibly annoying) guys.  Believe me, sugar, she’ll be a lot happier in bed with a guy who admits he doesn’t know anything than a blowhard who pretends he does, but doesn’t.  You say you don’t know how to give oral sex?  Well, you’re in company with at least 80% of the male population there.  Ditto not knowing how to guide the dance; that usually ends up being the woman’s job.  And unless you have an actual micropenis, don’t worry about being big enough to satisfy her; if she were a size queen she’d already have asked you about that.  Though your fears are understandable due to the garbage you’ve taken in from both your upbringing and the popular culture, it is a virtual certainty that they are baseless:  you aren’t going to lose her because you aren’t Superstud with a magic penis (especially because there ain’t no such organ).  That would be true even if you had a typical level of experience for your age, and it’s even more so since you were upfront about your lack thereof.  Relax, have fun, and let me know how it goes.

(Have a question of your own?  Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

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It’s not clear why WhatsApp settled on such an oddly specific number.  –  Doug Boulton

This week’s seasonal video was contributed by my friend Frank, who has a knack for finding such things but won’t get on Twitter.  The links above it were provided by Nun YaTim CushingMistress MatisseRadley BalkoEmma Evans, and  Clarissa, in that order.

From the Archives

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