From time to time readers of my pretty dumb things write and ask me advice. I have provided one reader with a D/s song list, another with a primer to anal sex in two parts (one & two), and yet another with my views on monogamy.
I like to think I can do some good from time to time, and in this altruistic spirit, I want to see what I can do to help my reader Tyler.
Tyler writes:
I am an eighteen year-old male and I couldn't help but get beyond off to your short publication on deep-throating. I want you to get the right impression here, I'm not writing you to be crude or inappropriate. I love getting head and have had quite some experience with it as well. Your narrative, though, made me incredibly envious. I have still yet to be deep-throated, let alone come close to finding a mate sharing your views on the subject. The girls I get with only have oral sex with me to satisfy me, and otherwise take no pleasure in it what so ever. I probably wouldn't care if not for my intense fetish of cock to mouth intercourse. I have even had fantasies of giving head and wouldn't mind experimenting with them although men in general do not turn me on. Do you have any suggestions of traits for me to look for in women that might lead me to someone who takes pleasure in sucking cock? Or any advice along the lines of what you look for in a worthy candidate? Or any feedback for me at all?
Somehow, deep-throating eighteen-year cock has been on my mind quite a bit lately. It’s nice to know that I share this interest with my readers who indeed possess said eighteen year-old cocks. It makes me feel, you know, in touch with the kids.
Kind of young at heart. Or at some other primal organ.
Let me give mad props to Tyler who at eighteen not only knows what he wants, but asks for help to find it. This kind of fearless spirit bodes well for you, Tyler. Rock on with your bad self.
And now, the advice. It seems to me that young Tyler juggles a few different dilemmas in his letter. The first seems to be feeling cool about loving oral. Which is kind of a no-brainer to me. I know it's cliché, but I must say it: I don’t have a cock of my own, but if I woke tomorrow and did, the very first thing I would do after peeing standing up would be to go out and beg, borrow or steal the best blow job I could find.
I have my toes sucked, and it feels sublime, but I have to imagine it’s not even a nano-sensation compared to what it would feel like to have my cock sucked. So for those of you men who feel squidgy about getting the oral, enough.
Lie back and enjoy it, babies. The same goes for your chicks.
The next issue that Tyler has is how to find a chick who likes to suck cock. I don’t think it’s something you can divine by looking at a chick. I don’t think the size of a woman’s mouth or the fullness of her lips or the wideness of her eyes can give you a clue into how she feels about wrapping her mouth around your phallus.
I could be wrong, and do let me know if I am. Not having a cock of my own, I’m pretty much going on second-hand evidence. If there is something short of an “I (heart) fellatio” t-shirt that clues you in to which women enjoy the cock suckage, do tell. I’m sure that Tyler and others would offer up to you their profound gratitude.
So how can a fine young fellow find a fetching fellating female? I hope I can help narrow the search.
Some happy cocksuckers like me were born; others were made. And the making takes time; therefore I would urge anyone who wants a woman who likes cock sucking to date an older woman. Ben Franklin was a wise, wise man, and his advice on dating older women is as helpful today as it was in 1745 when he wrote it. We women of a certain age know what we like and we aren’t shy about enjoying it. (Although drawing on my own experience, I would suggest to Ben that those who are grateful are often the younger men.)
If you want to enjoy sex with a woman find a woman who enjoys sex. Sadly, the way that women are built by nature and the way that we are made by culture often keeps us from enjoying sex in our full capacities until our thirties.
Therefore find yourself a nice thirty year-old, or older, woman who wants a younger lover. We abound. We often advertise. We’re looking for you. And more germane to the topic, we know how to get on our knees and worship your phallus like you’re a Roman General. Additionally, what we want from you is mostly friendship and hott sex, which can often free up the whole emotional brou-ha-ha about the erotic experience.
Moreover, you might learn something in the process. (Two strong reasons for dating a teacher: We like to teach and we have older woman/younger man fantasies. If you’re not jailbait, it’s win/win for everyone.)
Lest we not forget, the woman you are with (or man, actually) can learn too. I was lucky in that I developed in pre-pubescence the ability to suppress my gag reflex (I had Strep throat a lot; I hated tongue depressors; I learned. It came in handy). If you want your lover to learn how to deep-throat, or you want to learn yourself, the first thing to do is to be not afraid. The very worst thing that will happen is that the suckee will puke and the mood will be lost.
It’s no big.
I promise that I will write you a step-by-step description of how I deep-throat, but I’ll do it tomorrow because this post is long. And because I want you to keep coming. Back.
The next issue that Tyler has is this lingering latent question of some hott boy-on-boy action. To which I have to say this: you only know once you try. I truly believe that a person’s sexuality is like a three-dimensional sliding scale. A human can move along the spectrum of hetero and homosexual acts, in and out of vanilla and rockyroad sex, up and down in levels of erotic desire. Judith Butler said that gender is fluid; I say that sexuality is. Ride the wave.
One thing about my sexuality is this: it changes. Often. And surprisingly. Change can be freaksome, but it's less so if you just give yourself the permission to make mistakes, in and out of bed. It’s cool to check out being with a dude and decide it’s not your particular brand of vodka. It’s cool to have to sample a few dudes and decide you’re bi. It’s cool to do it all and figure out that it depends on the person, the moon, the biorhythm, the whatever.
In the end, my advice about sex always comes down to this one word over and over and over again: talk. Talk about it. Talk about what you want. Talk about what makes you feel good and why. And then listen to your partner tell you the same. It can feel very weird and alien to talk about sex, but I promise you on all things sacrosanct that if you and your partner can learn to talk about sex, you can learn to talk about anything.
Talk is not cheap. It’s the most valuable thing you and your partner(s) can do.
Although a well-sucked cock, that’s a good thing too. A very good thing indeed.
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"It's a good thing." What would we do without our Martha Stewart of sluttdom, our Emily Post of anal? It's Chelsea Girl's friend O, adding an appeal for funds. For just pennies a day, we can help CG pay her rent. So drop some pennies in her tip jar, and support her pretty dumb things. It's safe and anonymous, and your credit card statement will just say "sixapart."
It's like a glory hole, but for money.
C'mon, you know you want to.




Yeah but the real question is, how can you find someone who's into butt-painting? ;)
Posted by: Lex Konrad | 20 December 2005 at 12:43 AM
i have a question on this subject. what's a guy to do and think about a girl who professes to be great at giving blow jobs, and loves giving them...but never does? just wondering...
Posted by: phillip | 20 December 2005 at 03:22 AM
I know I've always had older women fantasies - since, oh, fourteen. Of course, that was likely due to the fact that the only women I came into contact with who had any clue as to those things I was interested in, were all way out of my age group at the time...
Phillip - my suggestion would be to call them on it. A lot of women I know take great pride in their cocksucking skills. Make it a challenge for them and they'll be on their knees in no time.
Posted by: Djaevle | 20 December 2005 at 10:25 AM
In my experience, women who wear tropical-colored lipstick like giving head and give it well. By "tropical-colored" I mean your hot reds and pinks.
Goth girls who wear black lipstick do not give head with any degree of enthusiasm, nor do women who wear conventional church-on-Sunday red lipstick.
Moreover, you can often tell a woman who likes giving head by watching how she applies lipstick. The ones who unsheath the mini-member and hold it before their eyes with slowburning appreciation before the applique are headgivers. Occassionally you spy a woman whose lipstick is actually shaped like a cockhead, and then you know you're onto something.
Posted by: Rup | 20 December 2005 at 01:50 PM
Lex, I guess you're the expert on that arcane tidbit of knowledge.
Philip, I'd definitely take D'j's advice. Though I must say that my rare lacklust fellatio arose from feeling resentment toward the man to whom the cock was attached, so you might look to the relationship for the spontaneous lack of head, especially if you've gotten it from the winsome lass preciously.
And Rup (not to be confused with the incredible austral Rups), I wouldn't be caught dead in lipstick. For me, it's lipgloss all the way, baby. It's shiny and slick and slightly sticky.
Sound like anything you know?
Cheers,
cg
Posted by: chelsea girl | 20 December 2005 at 03:29 PM
"Somehow, deep-throating eighteen-year cock has been on my mind quite a bit lately. It’s nice to know that I share this interest with my readers who indeed possess said eighteen year-old cocks. It makes me feel, you know, in touch with the kids."
Born two years too late it seems! :)
Posted by: Austin | 20 December 2005 at 06:03 PM
Tyler - you can also make a deepthroater even out of the straightest woman. I am having a relationship with a early-30ish married woman that basically never gave head before. Over several months I gradually got her into porn (and there's a lot of 'hang your head over the bed and slide it in' deepthroating going on there). See if you find an older woman who's open minded towards porn, then slip some deepthroating vids together. Jayna Oso or Lucy Lee are great talents.
Let your jaw drop and gasp in front of her when the phallus is engulfed on film, and she'll know what it takes to really trip your switch. Either she'll start practicing on her own and try it on you, or you can look for another. If she tries she'll gag a lot so don't force it in - let her lead. Soon be able to take it all the way to the your kiwis, and at that point you can get into pumping like it was intercourse. (Getting chills just thinkin of her)
And there is absolutely NOTHING in the world that feels better than when your tip pushes past the mouth into the sacred canal.. ahhh. Gotta make a phone call!
Posted by: 'twon | 20 December 2005 at 10:56 PM
I agree with c.g. communication is the key. My girl is quite a bit older than I am, and yes I get my way with most things that I want. I simply am patient and don't push until it is time. Blow jobs are nice, but so is getting laid, take it slow and be nice. Also, from my experiance gay guys like to give "nice" straight guys B.J.'s. Tyler if your curious then maybe that is something to try. Remember be nice!
-Early
Posted by: Early | 20 December 2005 at 10:57 PM
thank you so much you really helped i've been trying so hard to force it down that i never concentrate. your advice was perfect for me and my boyfriend thanks again
Posted by: amanda | 15 October 2006 at 10:00 PM
I'm in a nearly identical position to Tyler (three or so years ago, that is) and appreciate your thoughts on it. It's a bit difficult for me to propose anything such as oral sex with someone so much older, let alone meet someone who qualifies for the job. I suppose craigslist will have to do for now.
BTW
I've never posted before, but I'm an avid reader of your's who finds your posts absolutely fascinating.
Best wishes on being published and finding the right career,
Cody
Posted by: cody | 03 August 2008 at 09:50 PM
God - I LOVE this blog! Just found it today. Wonderful writing style and the info is spot-on.
I AM one of those mythical deep-throating chicks. I guarantee that no one could tell without help on my part. I look conservative, don't wear tacky bright lipstick or nail polish, dress well, and seem like the nice lady next door. Lady in the streets, freak in the sheets as the saying goes. So don't waste time trying to figure out the "type" because it's just not possible. I love blowing a guy's mind the first time I pull him all the way into my throat and pop him in and out. God... makes me wet just to think about it.
Posted by: Kris | 15 December 2008 at 09:31 PM
hmmm . . . I've had my toes sucked and it does feel similar to having my cock sucked - if you were to conflate (is that the word?) the sensation of your toes being sucked with that of your clit being tongued, you might approximate the sensation that you and your blessed sisters provide us through fellatio, although, not posessing a clit, I can't say for sure.
Beyond that I just want to say what a pleasure it is to read such articulate and sexy stuff from a woman - I'm so glad I stumbled across your blog. Thanks!
Dave
Posted by: Dave | 23 December 2009 at 04:06 PM