Sex: Your Questions and Answers

This week is dedicated to reader questions. Feel free to send along any of your questions about sex, relationships, sexuality, or sexual health. The nastier, the better. The tamer, the better. Anything you got, I’ll answer. You can submit questions by sending me an email directly or by just asking me in person. You’re promised my strictest confidentiality.

Question: I’m 21 and I’ve never had an orgasm!!! I know that it’s harder for women to orgasm, but all my friends constantly talk about how great the sex is that their having and about the all the orgasms they have. It makes me feel incompatible and like something is wrong with me! All my boyfriends have tried to find my g spot and perform oral but nothing works! The most recent guy I’ve been sleeping with can last a long time in bed but even the extended sex sessions don’t bring about orgasm. Is my vagina broken!?!? I don’t know how to fix it! Any advice?

Your vagina is not a tinker toy—if it doesn’t shake when it’s wound up, that doesn’t mean that it’s broken.  Vaginas are as individualistic as the people they belong to. So, just because your friends overflow their pink pipes regularly doesn’t mean that you should perceive your inability to do so abnormal. In fact, a large chunk of women in America have never had any kind of orgasm, fewer women have experienced orgasm through penetration only, and far fewer women have experienced female ejaculation.  The statistics are all over, but one study estimated as many as 36% of women in America have never reached orgasm. You are not alone.

I know that it can be frustrating when your slobbering bulldog won’t behave. But you can’t expect to give your pink puppy unprecedented commands and receive obedience. The key to taming it is training it.  I always say that sex with a partner is more pleasurable when you’re well practiced in auto-sex. The reason for this is because you’re able to discover what you find pleasurable, practice those things on yourself, and train your body to respond to those actions. It seems as though you’ve been depending on your lovers to make you come, but you’ve never spent some time in the hole yourself. What you need is some good ol’ fashioned masturbation. It can be a bit difficult to come under the gaze or expectation of a lover. Especially if you’ve never had an orgasm and you’re working yourself into a frenzy over it which, judging by your excessive use of exclamation points, you are. Just calm down and take some stress-free touchy time for yourself.

Because of the difficulties you’ve been having, I suggest focusing primarily on the clitoris, at least in the beginning. Many women who have trouble with climaxing find that focused stimulation helps them get over the hump (and onto another). Exclusively stimulate your clitoris–feel around to see what feels nice. Once you find a particular spot, focus your physical stimulation there. You may opt to use a vibrator or some textured materials to aid on your solo excursion to the slushy South Pole. That’s fine. In fact, women who are usually harder to get off cannot come without some more intensive stimulation. I suggest buying a small bullet vibrator—you can find one on Amazon for less than ten bucks—or covering your hand with a textured cloth. You can also try changing positions. As you’ll see, a change in position can greatly alter the experience of a sensation. Another thing that will help you tremendously is some smutty material or thoughts. The more turned on you are, the easier you’ll get off.

Only trial and errection will allow you to discover what works for you.  Once you have your first orgasm, note the conditions of this orgasm and try to replicate them another day. Try to discover what exactly is doing it for you—is it the position, the vibration, the fantasy—and make some clit-cliff-notes for your future or current partner(s). For further advice on masturbation, see my column on self-love on the Phoenix website.

Lastly, don’t worry so much about it.  Your professor isn’t going to judge your kitty petting abilities (unless you stumble into my wildest fantasies). There are no consequences for taking some time to figure out your body, only benefits. Think of this as a fun and sexy task that will ultimately lead to something wonderful. You’ll know just how wonderful soon enough.

Question: How many penises fit into a butt?

Is this a riddle? A math problem? Well, butt sex isn’t Janga and it sure as hell isn’t calculus. There is no equation that I can give you that will calculate the ratio of penises in anus by square ass.

If you’re asking because you’re serious about having multiple penises in your ass, all I can say is that you need to discover your own threshold. My suggestion is to work on your (or whose ever’s) butt skills. You should be in good practice for basic anal sex before you start trying more extreme things. It is possible, with lots of practice, to get your anus to stretch to amazing girths during sexual intercourse. But, you’re definitely not gonna want to try this casually or without working up to this moment of multiple cocks in the pit. It’s difficult enough to get one penis up there, nevermind multiples penises. So, just work on that for a while. Start by regularly inserting an average sized dildo into the ass.  You may also want to use a butt plug for a few hours a day to acclimate your sphincter to this type of work out. Increase size as the weeks go on. Have lots of patience and lots of lube. On that magical day when your fantasy comes true, it will be important to start slowly, relax, and ease into the process, inch by inch, dick by dick. For finer details on anal sex, refer to my column on penetrative sex on the Phoenix website.

Believe it or not, taking time to get your ass in shape may not be the hardest thing with a fetish like this. The trickier part will be finding a group of guys that are willing to allow their wangs to be painfully smushed together by your anal sphincter. You may opt to use multiple dildos instead—possibly operated by many people. I don’t know if that will have the same effect on your sexual psyche, but it may be worth a try as this is a harder to realize fantasy.

If this alternative doesn’t please you, you should seek advice from others who share your fantasy and have been able to satisfactorily realized it. A community of people with this exact fetish does exists (as does porn, I’m sure) somewhere on the internet. Get your hands a little dirty and do some research. Google: ‘anal gang-bang’, ‘brutal anal’, or ‘extreme deep ass stretching’  and see where the these sites take you. You can find instruction guides, appreciation blogs, or, really, anything else you would (and even something that you would not) want to find concerning this fetish through message boards.  You might also find willing participants/contemporaries/like-minded  friends/generally interested parties  in communities that fetishize humiliation, pain, and deification. Set a wide net.

Having said all that, if you just wrote in for my estimate on the average butt and not an answer concerning kink, I would say no more than two penises of average girth.

Question: If you could sleep with anyone on campus, who would it be?

Any of my professors–I like my partners sadistic.

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