I directed three new sex-ed shorts—on cunnilingus, fellatio, and the G-spot—for the fabulous feminist sex shop and site The Smitten Kitten. They star me, Dylan Ryan, and Danny Wylde and you can watch them for free here. I’m very proud of how they turned out, and can’t wait to hear what all of you think. In addition to some solid information, there is super hot sex—er, demonstrations—by Dylan and Danny. This was the first time these two had ever worked together, which is always a totally mystery going in. As it turns out, they have insane can’t-keep-their-hands-off-each-other chemistry. We shot so much good stuff that we had plenty left over. So, in addition to the sex ed shorts, you can purchase a full sex scene, “Dylan + Danny: Extra Credit,” on demand. Photos above are by Clare from The Smitten Kitten who was on set.
I’m a 19 year old student at the University of Chicago. My not-so-problematic problem is that I’m something of a sexual perfectionist, when it comes to pleasuring my partners. Therefore, worried that I must be missing out on an excellent means for pleasuring, I’ve decided that it would be good to keep a vibrator or dildo handy. The only problem is that I don’t know how to use such a device. It’s not very intuitive for me, and most of the women I’ve slept with have had no experience with them either. So, can you tell me an effective vibrator technique, or where I can find out about it?
Bravo! I wish every guy was as smart and self-confident as you are to have a toy handy to please his female lover! When choosing a vibrator—especially if it’s your first one—I absolutely recommend a trip to the sex toy store. You can see them, turn them on, feel the vibration, listen to the noise they make, and see what might work best for you. Since this isn’t for a specific woman, select one with variable speeds that could appeal to different preferences. Test the waters by exploring all different areas of her pussy with the vibrator first. Remember not to go directly for her clit with a vibe before she’s had some warm up with your hand or mouth first. Vary the speed, pressure, and position of the vibe—she’ll let you know when you’ve struck gold. Once she’s worked up, she may want you to stop wandering around with it and stay in one place for a while, so be prepared to stop dawdling and get down to business. Vibrators can help you be in two places at once when she uses it on herself to add clitoral stimulation to vaginal or anal penetration.
My girlfriend and I have both used Pyrex toys and love them. Our local store has a dildo for strap-ons that is made of blown glass. It sounds awesome but I was concerned about safety. Could it break or even shatter? Which glass toys are safe?
—Crazy but Cautious Over Glass
Dear Crazy but Cautious Over Glass:
Glass sex toys have gotten incredibly popular in the last few years, and it seems like they are everywhere. Glass toys can be easily cleaned and sterilized, since they’re non-porous, and they are compatible with all kinds of lube. Plus, there smooth texture feels amazing! But I agree that it’s difficult to tell if a glass toy is safe or not. “Blown glass” only describes how the toy was made (it was hand blown) not what kind of glass is made of. You should ask your local store or web retailer who made the toy before you purchase it and do some research on the company. Ultimately, you’re looking for a toy made of medical grade borosilicate glass or Pyrex, a brand name which has become synonymous with heat and shock resistant glass. A properly made toy of borosilicate glass can withstand up to 3,000 lbs. of pressure as well as extreme heat and cold. Certain well-established, reputable companies guarantee that their toys are made of Pyrex or borosilicate, including Phallix Glass, XXX Glass, XHale, and PyreXions. Babeland and Good Vibrations, and Glass Fantasy have a good selection of unique glass toys. To protect your glass toys, always clean them promptly and store them in a soft, padded bag to protect them. And if you ever find a nick, stop using the toy immediately.
My girlfriend has an insatiable appetite for sex. We often have it once a day, and, if not, she masturbates. We both enjoy anal stimulation and have a collection of varying size toys. However, my girl uses them daily. Can someone have too much anal sex or anal toy play? Is it okay to do it almost every day?
You’ve got one of those problems that lots of other readers wish for! It is absolutely safe to have anal penetration every day as long as you are doing it safely and responsibly. That means: plenty of warm-up, lots of lube, and stopping if you experience any pain. The key for your girlfriend is to listen to her body. As long as everything feels good, she doesn’t rush the process (which even experienced players can do), and she takes a break if she’s sore, she will be fine. Obviously, if she starts to experience anything significant, like cramping, bleeding, or discomfort, she needs to stop and see a doctor.
My fiancé and I have been exploring BDSM, which we enjoy fully. He wants to have anal sex with me, and although it would be the first for me, I’m willing to try it out at least once. He does have a really big penis — gloriously big — and I’m concerned about the process as I’m a small woman. Is there anything I can do to prepare myself for him and make this enjoyable for both of us?
–Tiny But Tempted
Your physical size does not necessarily correlate with your ability to take a “gloriously big” cock up your ass. I’ve seen women who are five feet tall and 98 pounds with very large things comfortably nestled in their behinds. It’s more about your internal than your external size. Like the pussy, the ass has the ability to expand when you’re aroused. Plus, the rectum is longer than the vagina and therefore can usually accommodate something bigger.
However, since your guy is larger than average, it means that you’re going to have to work your way up slowly. And since it’s your very first anal adventure, his cock should not go into your ass all in one evening. Instead, I recommend that you begin playing with a finger or a slim toy either alone or with him. Use plenty of lube, go slowly, and stimulate your clit. When you’ve practiced a few times with the one finger/small toy, and it feels great, you can move on to two fingers or a slightly bigger toy. Again, you can play together or you can add anal play to your masturbation. The important thing is not to rush the process. Find a dildo that’s “one step down” from your man’s cock. When you’ve worked up to taking that dildo, and it’s comfortable and pleasurable, then you can try his cock. Make sure he goes very slowly, and that you give him lots of feedback about how it feels. If you both take your time and let your ass set the pace, it will reward you in the end!
My boyfriend and I recently discovered the pleasure of penis pumping, and I’m thinking of getting a vaginal pump. But lately I have been using my guy’s penis pump on my asshole, and I love the sensation and the feeling. I was wondering if you have ever done this, and if it is a safe practice?
Many men and women have discovered the joys of pumping. For readers who may not know about it, a penis pump works like this: your cock goes inside a hard plastic cylinder which either has a built-in pump or an external one. As you pump, air is sucked out of the cylinder, and the vacuum-like suction sends blood rushing to the cock. This helps the cock become erect, enhances an erection by giving it a bigger appearance (temporarily), and creates a sucking sensation which many men love. Women can use the same pumping mechanism with the nipple attachment (a much smaller cylinder), which works great on the clitoris. There are also pussy pumps on the market made especially for women. The same principles apply: blood rushes to the clit, making is more swollen (and often more sensitive) than usual. I’ve pumped my own clit, and find that not only is it hot to see my clit all fat and thick, but clitoral stimulation is a lot more intense after I’ve pumped.
I’ve never used a pump on my butthole. The puckered skin of the asshole is sensitive tissue that’s incredibly rich in nerve endings and gets engorged when you’re aroused much like the rest of our genitals. So, it makes sense that when you apply suction to it, blood rushes to the area and creates a pleasurable sensation. Similar cautions for all pumping apply: use a little lube inside the cylinder for a comfortable, easier fit; be careful not to pinch the delicate skin when inserting it into the cylinder; do not over-pump or leave the cylinder on for too long.
I love anal sex — much more than vaginal. I love the pressure just before the head pops in and that little ache as it does. What I am having problems with is that everything that goes in my ass seems too long. It feels almost like the dick or the toy is hitting something inside of me, and it hurts. I have a friend I play with and we do a lot of BDSM scenes, especially rape scenes and punishment-type scenes. He would like to see just how much my butt can take, and I do love the width of everything, especially the next day. Can you help me with the length problem?
Unlike the vagina, the rectum is not a straight tube. It has a gentle curve, first tipping forward toward the front of the body, then away, then forward again. Everyone’s curves are different, and some are more pronounced than others. As a result, if you stick anything straight inside the rectum, you can wind up hitting the rectal wall, which is not a good feeling for anyone. It sounds like that may be the sensation you described. Have your partner experiment with different positions and angles when he fucks you in the ass, and see if there’s one that allows for penetration without the pain. Toys made of flexible materials are more comfortable and bend easier with your curves; if a toy itself is curved, the curve should be aimed toward the front of the body. All that said, you can also have a short rectum. Since you get pleasure from wide toys, I say invest is some short but wide dildos or butt plugs — go with what works!
Do you recommend using inflatable dildos to stretch the rectum?
–Ready to Blow Up
I don’t recommend anything to literally stretch the rectum. Toys are a great tool to teach the ass to relax and open up, to get it accustomed to being penetrated, and to warm up for more. It’s not stretching as much as it’s expanding, since the rectum has the ability expand when a person is turned on and relaxed. Inflatable dildos and butt plugs are a fun toy to play with, and they are also a great way to gradually increase the width of a toy you can take in your ass without investing in a new one. Make sure you inflate the toy before you put it in your ass to measure its limit, then you can gradually work your way up from one pump to several pumps!
I started doing anal play about ten years ago. It was somewhat uncomfortable, but I persisted. Well, my persistence paid off. I am now able to take a dildo about 10 inches long and about 7.5 inches in circumference. I thoroughly enjoy it, but I have a question about how deep you can go. I tried inserting it to about 12 inches, and I got it worked in, but after about five minutes, I removed it, and there was blood. It shook me up big time. It stopped immediately, but I didn’t insert anything for week for fear of starting something I couldn’t stop. I felt no pain and it felt good. Is the blood a big deal?
Since the rectum is quite delicate and covered by mucous membrane, even the gentlest of penetration with the smallest of toys can cause a small tear and a little bit of blood. It’s usually not cause for concern as long as the amount of blood is small and there’s no serious pain or discomfort. However, in your case, you’re using very long, thick toys for penetration that give you more of a chance of causing an abrasion or tear; you must realize that a twelve-inch dildo or one that is nearly eight inches thick is huge and not common. When you penetrate your ass with something longer than about ten inches, you move beyond the rectum into the sigmoid colon, which is made up of fragile tissues. Technically, anything bigger than 10 inches could perforate this, especially if it’s inflexible. Plus, an extremely thick dildo can stress the rectal lining. My advice is that at the first sign of blood, you should stop immediately and give your ass a few days to recover. If these big dildos continue to make you bleed, then I suggest you select smaller ones.
I’m a guy, I like women, and I’ve never been attracted in any way to men. I want to try anal sex (with me on the receiving end) with dildos and even a strap-on. Does this action means I am gay? I have heard that men can have orgasms by prostate manipulation. How would my wife be able to do this to me? Is there a specific method or do I just hope that she does it right?
–Wanting But Wondering
The idea that men who like getting it up the butt are gay is absolutely a myth, one fueled by our society’s homophobia and misconceptions about anal pleasure. Plenty of heterosexual men enjoy receiving anal pleasure, whether with tongues, fingers, or toys. As I’ve said before, anal sex can be an incredibly powerful experience, but it’s not powerful enough to change your sexual orientation! I think that men who enjoy strap-on action especially have anxiety because of the implication that they are getting fucked by a cock, whether it’s silicone or not. The truth is that it feels good, and when you turn around, you want a woman on the other end of that cock.
Men can definitely have orgasms through anal penetration. The prostate gland is about an inch to an inch and a half inside the rectum on the front wall. So, if your wife slips her finger inside and heads toward the front of your body, she’ll find an area (about the size of a walnut) that feels differently textured than the rest of the rectal wall. She should gently rub the spot as you give her feedback about how it feels. Every guy is different, so your communication is critical to helping her stimulate you in exactly the way you want. As you get more aroused, the prostate will swell and become more sensitive. For prostate stimulation with a dildo (whether strapped on or in her hand), select a curved toy and make sure the curve is always toward the front of your body. Some guys like to have their cocks and balls played with, others want anal play alone — that’s something for the two of you to experiment with.