Sep 112013
 

My girlfriend and I have just discovered anal sex and enjoy it a lot; I really enjoy having my cock in her tight asshole. But there’s one thing I want to ask about: the next day after anal sex, I have a painful backache. We do the ‘spoon’ position, and while it is happening, I don’t have any pain at all. Do you know anyone else with this problem and do you have any advice for me?

–Want to Get Laid, Not Laid Up

Welcome to the wonderful world of anal sex! It sounds like you would be off to a pleasurable start except for the painful aftermath. My first impression is that this is probably muscular pain. When you start a new sexual activity, you use a bunch of muscles you’re not used to exercising on a regular basis; just like if you started a new work out regime at the gym, your body needs some to adjust. It may simply be a matter of awakening those muscles and getting them back in shape.

It could also be the position you’re in is putting strain on your lower back. The next time you do it, try to concentrate on your body movements and see if the position is uncomfortable for you; perhaps you only need to make a slight angle adjustment and it will feel better. You can also do regular stretching and simple exercises to avoid muscle strains. Find a personal trainer, physical therapist, or someone knowledgeable about working out and ask them to recommend some exercises for strengthening your lower back. Once you get your back in better shape, there will be no stopping you.

May 152013
 

My lover and I would like to experience pleasurable anal intercourse. The only previous experience I had was a painful 5 seconds, 10 years ago, when my ex-girlfriend and I hadn’t the least notion of what we were doing. Since then I’ve read several reputable sources on the subject including your book and the work of Dr. Jack Morin, and I seem to recall some advice regarding facilitation of penetration. I remember reading a recommendation somewhere that the person receiving the penis or dildo, lie on a certain side of their body in order to more easily allow for the natural curve in the sigmoid colon, where it’s attached to the rectum. Was this simply my imagination playing tricks on me? Am I getting this confused with stuff I read right before I had my first digital rectal exam and a colonoscopy? Or is there in fact a “correct” side to be lying on?

–Side Seeker

On the instructions that come with a store bought enema, one recommendation for a comfortable position (sometimes called the “Simms Position”) to give yourself an enema is to lie on your left side and bend your right leg toward your chest. This position allows easy access to the anus, keeps the weight off your abdomen, and allows the enema solution to flow easily into the colon. Likewise, often when you are given an enema from a health care professional, they may put you in that position. But I’ve never heard of a sex educator recommend that someone lie on a certain side for anal penetration.

When it comes to anal penetration with a penis or dildo, your concern is about the rectum, not the colon. The rectum is slightly curved — which is why careful penetration is important so you don’t bump into the rectal wall — but its curves are not like the more drastic curve between the rectum and the sigmoid colon. You can receive and enjoy anal penetration is many different positions, including missionary, on top, spooning, doggie style, standing, bent over something… you get the picture.

I looked in Jack Morin’s book, Anal Pleasure and Health, and the only thing he says that relates to your question is: “Any position which places your legs at right angles to the upper body . . . will straighten the rectum a bit.” Again, this comment is in reference to a discussion about the curves of the rectum, not the sigmoid colon.

Apr 252013
 

photo(2)
I gave my Sexploration lecture at Bucknell University on Tuesday April 23, and there was a huge crowd. I often do anonymous questions at college events where students write their questions on notecards and everyone has to write something, even if it’s “no question.” The anonymity gives folks the freedom to ask their most pressing questions. I only had time to answer about 60% of the questions, so I’m answering the rest here. I’ve combined some questions that are on the same topic.

Is it weird that I want sex all the time even though I’m a virgin?
No. It’s common to have sexual desires regardless of your sexual experience. Remember what I said about the problematic concept of virginity? I encourage you to define sex as broadly as you want and not buy into the cultural construction of virginity.
Recommended: The Purity Myth: How America’s Obsession with Virginity Is Hurting Young Women

How often do most people masturbate?
It varies wildly from person to person, and how often just one person masturbates can vary depending on their energy level, desire, stress, opportunity, etc. There are some interesting stats you can check out. In general, I don’t think masturbation is ever a bad thing. Everyone should have a sexual relationship with themselves, and it’s a great way to figure out what you like.

I masturbate so much it’s turned into a chore; any tips for spicing it up?
Masturbation shouldn’t be a chore! But people can get into a repetitive rut. Don’t think of it merely as a quick way to get off, think of it as a date with yourself. Try changing positions, experimenting with new stimulation techniques, adding lube and a toy to the mix.

How long does it take to give a guy a blow job?
There is no set amount of time that it takes anyone to do anything sexual. If you’re giving the blow job, take charge of the situation and do it for as long as it feels good, for as long as you want to. If you get tired or overwhelmed, switch to using your hand or doing something else.
Recommended: The Expert Guide to Oral Sex 2: Fellatio

How long should a guy last during a blow job?
I hate to repeat myself, but: there is no set amount of time. Depending on the guy, the stimulation of oral sex could bring him to orgasm slowly, quickly, or not at all. Blow jobs do it for some people and not for others.

How nutritious is semen and how can I convince my girlfriend to swallow?
Semen has little to no nutritional value because you don’t ingest all that much of it. You don’t want to convince anyone to do anything they don’t want to do. You can share your desire with her and tell her why it turns you on, but ultimately, it’s her choice to swallow or not, and you’ve got to respect it. Also, swallowing semen is a riskier practice in terms of safer sex than not swallowing, and I am a fan of condoms for blow jobs.

How do you improve oral sex?
Since you didn’t specify, I’m going to make some statements that apply to all kinds of oral sex (cunnilingus, fellatio, and analingus), then give you some particulars. Enthusiasm, focus, tenacity, and paying attention to your partner’s body language are all good qualities to have when giving oral sex. Use your fingers and hands along with your mouth. For cunnilingus, experiment with different techniques using your lips, mouth, and tongue, and ask your partner to tell you what she likes (if she doesn’t know, explore and ask her to alert you when you’ve stumbled on something great). For fellatio, concentrate on the head and the sensitive frenulum on its underside (remember our anatomy lesson); experiment by applying different amounts of pressure with your mouth along the head and shaft. For analingus, use your tongue and lips to get into the folds of the sensitive anus.
Recommended: The Expert Guide to Oral Sex 1: Cunnilingus, The Expert Guide to Oral Sex 2: Fellatio, and The Expert Guide to Advanced Fellatio

I don’t think I enjoy sex at all. The picture of the vagina (in your presentation) made me squirm, and I have one. What can I do to be comfortable and enjoy the experience when my partner wants to have it?
First, this is a question I can’t answer with a pithy one minute (or three sentence) response. It was a line drawing, but an explicit one, of a vulva, and we are not used to looking at those images on the big screen or in public, so it can make some people uncomfortable for a number of reasons. But you said you don’t enjoy sex at all. Could you be asexual? If you have sexual desire, then it’s a matter of getting comfortable with your body and with sex. Do you masturbate? It all begins there, so I’d start with establishing a sexual relationship with yourself before you address sex with a partner.
Recommended: Sex for One: The Joy of Selfloving

What is the best way to have sex in a long distance relationship?
I assume you mean when you and your partner are apart? Use technology to keep you connected. Dirty text messages, naughty instant messages, steamy emails, and Skype with mutual masturbation. I caution you against sending naked or sex pictures to each other, however, since we’ve seen all the trouble that can cause.

Got any good positions?
Each position has its pros and cons, and experimentation is key. If you like Missionary, try Flying Missionary where the person on their back puts their feet on their partner’s chest. If you like Cowgirl, try Froggie where the person on top balances on their feet. If you like Doggie Style, try Tailgate, where the receiver lies on their stomach and the penetrator then lies directly on top of them.

Do you have tips for using a toy to stimulate the G-spot?
Pick a curved toy like Pure Wand, and always aim the curve toward the front of the person’s body. Many G-spots respond to deliberate, firm pressure rather than gentle stroking, so don’t be afraid to apply pressure—just make sure your partner is aroused and ready before you do.
Recommended: The Secrets of Great G-Spot Orgasms and Female Ejaculation and The Big Book of Sex Toys

Does size matter?
The easy answer is no. People are way too wrapped up in penis size, when most folks want a compassionate, responsive lover more than a particular size. But I don’t want to deny that everyone has different tastes and turn ons, and some people do like penetration with big stuff. But that’s why God created dildos.

How do I get a vibrator and which kind do I get?
If possible, visit a sex-positive store like The Smitten Kitten, Good Vibrations, or Babeland. When you shop in person at stores like these, the toys are out of their packages, so you can see and feel them, feel the vibration, hear how quiet or loud they are, plus you benefit from the advice of experienced sex educators who work there. If that’s not possible, try one of their websites; they all have detailed product information and customer reviews.
Recommended: The Big Book of Sex Toys

I’m a girl. Do I need to shave my pubic hair before I have sex?
Your pubic hair is your business! It’s a matter of personal taste, just like how you cut and style your other hair. Some people let it grow, others trim it back, and others wax or shave some or all of it off.

As a female, how do you know if you’ve had an orgasm?
I want to say, “Oh you’ll know!” but I want to be more specific. Some of the physiological responses include: a feeling of release; muscle contractions of the uterus, vagina, and sphincter muscles; other muscle contractions and muscle tension throughout the body; involuntary muscle responses that cause you to make strange faces; and cramping of hands and feet. Talking to your peers about what their orgasms feel like is a great way to open up a conversation and hear from real people about their experiences.
Recommended: The Expert Guide to Female Orgasms and The Ultimate Guide to Orgasm for Women: How to Become Orgasmic for a Lifetime

How long does it take a woman to climax?
There is no set amount of time, and I hesitate to even say there is an average amount of time. Women often put pressure on themselves about this (I hear all the time “It takes me a really long time,” or “It takes too long”). Concentrate on what’s going on and how it feels, and don’t think about the clock and how you measure up to it.

Do you have any suggestions for mixing things up during sex?
Lube. Sex toys. Role play. Analingus. New positions. Porn. Do anything except intercourse. Mutual masturbation.
Recommended: What You Really Really Want: The Smart Girl’s Shame-Free Guide to Sex and Safety

Do you poop when you have anal sex? How do you have “clean” anal sex?
When you have a bowel movement, feces stored in the colon pass through the rectum, down into the anal canal, and out the anus. The colon is the storage area, and the rectum and anal canal are pathways. If you have good bowel habits and plenty of fiber in your diet, then there should be very little fecal matter in the rectum and anal canal. When you play with fingers, a toy, or a penis, you’re not going beyond the rectum. Go to the bathroom before anal play. In addition, take a warm, soapy shower or bath before anal sex to make sure your genitals are clean. You can even slide a soapy finger into your anus. Always use the most mild soap you can—either a castile or pure glycerine. A trip to the bathroom and a shower will go a long way toward you having relatively clean anal penetration. I say “relatively clean” because I want you to be realistic. There are no guarantees in life, and some amount of fecal matter may be present in someone’s rectum. If you want to go the extra step to make sure you’re totally cleaned out, you can give yourself an enema beforehand.
Recommended: The Ultimate Guide to Anal Sex for Women

How safe is anal sex and how do I avoid anal fissures?
I always recommend that people use safer sex barriers if they are not currently tested and in a sexually monogamous relationship. You can transmit most sexually-transmitted infections (including gonorrhea, chlamydia, syphilis, HPV, genital warts, herpes, and HIV) through unprotected anal sex, especially penis/ass intercourse. In addition, as I said in my presentation, the ass is made of delicate, sensitive tissue which is susceptible to small tears or anal fissures. The best way to protect against them: use gloves to make your fingers butt-friendly, use plenty of lube, focus on warm up and don’t rush penetration, and, as the receiver, listen to your body.
Recommended: The Ultimate Guide to Anal Sex for Women

Is it inappropriate to go up to someone and say, “Wanna fuck? Right here, right now?” (I’m female.)
I like people being direct about what they want. I appreciate shameless assertion of your desires. So I don’t think it’s inappropriate to speak your desires in the right context with potential lovers. But, that said, there are repercussions for women who speak openly about their sexual desire, so you’ve got to take those into account, knowing that reactions to your honesty will be mixed (see next question).

How can I, as a woman, express wanting to have sex without looking like a slut?
Just do it. Own it. Don’t let anyone shame you for your sexual desires, experience, or consensual behavior. And don’t shame other women for theirs. Don’t buy into our society’s double standards that applaud men for their sexual prowess and punish women for the very same behavior. (Easier said than done, I know.)
Recommended: He’s a Stud, She’s a Slut, and 49 Other Double Standards Every Woman Should Know and What You Really Really Want: The Smart Girl’s Shame-Free Guide to Sex and Safety

How do we as a society combat false sex information like the “What Not To Do Guide to BDSM,” aka Fifty Shades of Grey?
You’re right, Fifty Shades of Grey is not an instruction manual, it’s a romance novel with some kink thrown in. But lots of people have read it and it’s opened up conversations about kinky sex, which is ultimately a good thing for society. If a friend mentions reading it or being inspired by it, be ready to let them know that it’s not a how-to and have recommendations for other resources that give solid information about BDSM.
Recommended: The Ultimate Guide to Kink and SM 101: A Realistic Introduction

I am really into bondage. How do I bring it up to a casual hookup without being scary and intense?
It’s all in the way you present it. Be direct and put it out there (“I want to tie you up” or “It would turn me on if you tied me up”) and make it clear that it’s a suggestion that your partner is welcome to embrace or turn down. If they agree, be prepared to give them information about safety before you start and always use a safeword.
Recommended: The Ultimate Guide to Kink and Midori’s Expert Guide to Sensual Bondage

How does a girl approach the idea of being a dominant with a guy?
Talk about roleplaying fantasies and see what kinds of scenarios you each come up with. Suggest some scenes where you play a dominant role and see what he says. Context is everything.
Recommended: The Ultimate Guide to Kink

Why do I have rape fantasies? It feels problematic.
Our fantasies often do not reflect our politics. Rape fantasies can be about exploring submission, masochism, surrender, objectification, control, and a slew of other dynamics. Although “rape” is the hot-button word in this question, the operative word here is fantasy. It’s a fantasy where you create the script, imagine the details, call the shots, and know how it ends—which is an entirely different thing than actual rape.
Recommended: Toybag Guide to Playing With Taboo and Mollena Williams’ two chapters in The Ultimate Guide to Kink

Any advice for a woman who wants to peg her man? Techniques, a particular toy, a particular position?
Pegging is strap-on anal sex where the woman is the giver and the man the receiver, and it can open up a whole new world of erotic exploration for couples. Great anal sex is all about the warm up. You’ve got to take your time, relish each sensation, and tease your partner into a frenzy before any serious penetration begins. As for toys, I love the Mistress dildo by Vixen Creations and any harness made by Aslan Leather.
Recommended: The Ultimate Guide to Anal Sex for Women and The Expert Guide to Pegging

What are your thoughts on tantra, sexual ecstasy and spirituality?
That’s a big question on a big topic. More and more people are getting interested in sacred sexuality, the intersection of sex and spirituality, sex magic, and Tantric sex. I want to refer you to two of the best, most accessible books on the subject: Urban Tantra: Sacred Sex for the Twenty-First Century and Tantra for Erotic Empowerment: The Key to Enriching Your Sexual Life.

How do you feel about porn, which often portrays false or fantastical situations? How realistic is porn? Is it misleading?
Well, it depends on the porn! Much of mainstream pornography portrays a fantasy and a performance, so there’s a lot of athletic positions, high energy and high libido, heightened reactions to stimulation, and earth shaking orgasms (both real and performed). You don’t often get to see honest communication, awkward moves, enough warm up before intercourse, a focus on other kinds of sex besides intercourse, partners being shy or quiet, stopping and starting, and much more. I like to portray more realistic sexual scenes in my films, where people verbally negotiate, ask for what they want, use lube and sex toys, focus on activities that turn them on rather than a “script” of how sex should unfold, get into positions that feel good for them, and allow enough arousal time and stimulation to allow female performers to have real orgasms. There are lots of feminists who make porn, and you may want to check out their films as well as films featuring real couples including Make Love Not Porn.
Recommended: The Feminist Porn Book

How can gender identity affect a sexual experience or a sexual relationship (even mentally)? How can we avoid gender identity becoming a point of contestation? We are both doms.
This question requires a longer answer, so I gave it its own Ask Tristan post.

 

 

 

 

Apr 182013
 

I want to create a scene for my submissive that combines anal sex and immobilizing bondage. She loves to get fucked when she is confined and can’t really move, and I adore seeing her in a compromising, vulnerable position. What can I say? It makes my dick really hard. My slave girl is pretty flexible, an experienced bondage (and anal) bottom, and she’s always game for lots of new things. I am hoping you can offer some suggestions for good positions as well as any safety concerns I should be aware of.

–Want A Helpless Bondage Bottom

Oooh, you two sound fun! Let’s talk bondage first. I’m not a rope bondage expert, so I’m going to recommend an easy kind of bondage using large, long leather bondage belts that you can find at Stockroom. Have your bottom stand and face you with her arms at her sides. Wrap a belt around her upper arms and torso (above her breasts), securing the buckle on one side of her arm. Do the same thing with a second belt around her stomach and arms between her elbow and wrist. Use a third belt around her waist and just above her wrists. Belt #4 goes just above her knees with a fifth belt around her calves. Move her slowly and put your slave face down on the bed (or the floor, if you’re feeling more sadistic). Secure the final bind: a belt around her ankles (you could also use ankle cuffs clipped together for her ankles). Now you have her in tight confinement and also a great position for anal sex. In fact, this is my favorite position and I re-named it in my book The Anal Sex Position Guide. It’s called “tailgate”: she lies face down on her stomach, and you straddle her and enter her ass. You could stay upright, and pull on the belts, using them as handles. Or you can lay on top of her. The combination of your weight on her and the bondage belts will make her feel truly immobilized.

If you’re interested in doing this with rope bondage, two great resources to see many different ties described and illustrated are famed educator Midori’s book The Seductive Art of Japanese Bondage and Jay Wiseman’s Erotic Bondage Handbook. I like Jay Wiseman’s “Split Lark’s Head,” for an arm/chest harness and on the bottom for mid-thighs and down, try his knee-to-knee and ankle-to-ankle bondage.

Oct 162012
 

My paramour seems to be preoccupied (to say the least) with the idea of anal sex. We’ve tried before a couple times, none of which ended well. I blame it on my own trust issues and the lack of lube. But it’s been a while and I’m feeling better (and braver) about it all. I recently read something about the possibility of semen finding its way from your anus to your vagina and impregnating you. I need to know if I’m gonna have to consider a contraceptive before allowing my beloved to go-a-spelunking in my magic cave without a raincoat! I’d hate to have to explain to my kid someday that he or she was conceived by mommy and daddy getting freaky in the butt!

–So Not Trying To Have A Butt Baby

First let me say that I am pleased that you’re willing to give anal another try — I promise you that lube will go a long way to making it a lot better! If I only received a question like yours once a year, I’d chalk it up to an ill-informed young person or an Internet jokester. But, believe it or not, I get at least one question about becoming pregnant from anal sex nearly every day. So let me reassure you that you’re not the only one who’s heard this rumor or is concerned about it.

Technically, the scenario you pose is possible, but it’s very, very unlikely and improbable. Semen would have to drip out of your ass and into your pussy and survive the transfer outside the body (sperm cannot live very long when exposed to air). Then, a cock or finger or toy would have to push the semen inside, so it had a shot at getting close to the cervix, through the cervix, into the uterus and fallopian tubes. It’s a long journey and beginning in another place doesn’t help matters for those poor sperm.

If you are seriously concerned but want to go condom-free, I recommend taking a few precautions. Have your partner ejaculate in your butt in a position where gravity is working in your favor, like missionary or spooning. As soon as he pulls out, make sure to have a baby wipe handy to catch any dribble and prevent it from migrating toward your puss. Use another baby wipe and give yourself a full swipe from front to back. That ought to cover you!

Feb 202012
 


The Expert Guide to Pegging: Strap-on Anal Sex for Couples comes out on Valentine’s Day!! Isn’t that just perfect? My latest instructional movie from Vivid-Ed stars Dylan Ryan, Wolf Hudson, Jiz Lee, Mickey Mod, Jada Fire, and Christian. This is not your mama’s pegging video, that’s for sure! The cast is awesome, their interviews and chemistry fantastic, and the scenes are the hottest strap-on anal scenes I’ve ever shot! Plus, there are lots of extras on the DVD. And, as always, if you buy it directly from me, you support your local feminist pornographer!

Feb 272005
 

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?

–Woodstock Girl

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!

Nov 082003
 

My girlfriend and I have tried anal sex multiple times, but she doesn’t like it unless I rub her clit. As soon as I stop rubbing it, she says it’s very painful and wants to stop. She is also afraid to try doing certain anal positions. We only do it lying on our sides, facing the same direction. She claims that doggy style hurts too much from our one time of trying it. I am desperate for help!

–Anal Addict Denied

It fascinates me that you consider yourself an “anal addict denied,” because you are, in fact, having anal sex — just not necessarily in the exact way you want to be. If your wife doesn’t like it doggy style, that’s most likely because that position offers the deepest penetration, and it obviously doesn’t work for her; fucking her in “spooning position” — which you say works for you — may mean less deep thrusting for you, but a lot more comfort for her. If you’re simply dying to do it to her doggy style, then I suggest taking more shallow strokes, and seeing if that feels better.

As for your problem that she doesn’t like anal unless you rub her clit, well, what exactly is the problem? Rub her clit! The majority of women need clitoral stimulation in order to orgasm, and most would say it enhances all kinds of penetration. I know lots of women who can’t take anything in their ass without something working their clit; it helps them relax, get aroused, and it just feels great. If rubbing her clit is difficult because of your body position, then let your wife work her own clit while you concentrate on her ass; that way, it’s a win-win situation.

Aug 022003
 

My husband and I have been experimenting with anal sex for a number of months now. We’ve had good experiences with butt plugs, anal beads, and other toys, but when it comes to anal intercourse, there’s always a problem. The initial penetration itself usually goes really well, but for some reason I can’t manage to have sex for any length of time at all. I mean, seriously, three or four thrusts, and I have to stop. It feels almost like there’s a second ring of muscle, farther inside that my husband is hitting when we have sex. Once he gets all the way inside, it’s fine, but when we start moving, he slips out past that ring again, and it hurts when he comes back through it. Am I imagining things, or is that really there?

Most of the time, if I lay still and concentrate, I can manage to relax everything enough for him to get off, but the second I stop focusing and start enjoying myself, everything tightens up again. It feels so wonderful having him inside my ass, I don’t want this to be something we have to give up because we can’t make it work. What do I do?

–Frustrated in Germany

You are not imagining things. What you’re describing makes perfect sense, anatomically. There are two sets of sphincter muscles, the external sphincters and the internal sphincters. For some people, these two rings of muscles are quite close together, but for others, they are farther apart. Both sets of muscles need to relax completely in order for anal penetration to be comfortable and pleasurable. They are like the “gatekeepers” to the ass, and penetration can be painful if you are nervous or tense.

You are doing the right thing by concentrating on relaxing, it’s critical to your enjoyment. You and your husband should experiment first with different positions; as you try several different ones, you can change the angle of insertion, the depth of penetration, and when he’s hitting that inner ring. He also needs to try more shallow thrusts, so that he doesn’t consistently pull out too far, which is obviously painful for you. I think your problem can definitely be solved with some creativity in positions and taking it slower.

May 282002
 

My husband and I want to try out anal sex really bad, but my problem is the pain — I know it’s not supposed to hurt, but it does. I keep telling him that missionary position is not the best for our first try. Is there another position you recommend? I really want to give this to him, but I am still very nervous. I have tried to relax, but nothing seems to work. I’m thinking I need a lube that desensitizes the area. I know if I can find the right kind of numbing agent, then I will do just fine. Do you know of any?

–Anal Chicken

You admitted being nervous about getting fucked in the ass, which is very common, but my question is: do you really want to do it? I sense a lot of reservation in your letter, and I am concerned that your fear and anxiety aren’t the only things holding you back. Your desire for this must absolutely be there (not just your husband’s), otherwise it’s not going to work, and it will continue to hurt. You are right that it is not supposed to hurt, and pain can be the result of many things: hesitation on your part; not being relaxed; not enough foreplay and warm up; not enough lube. You need to take it slow, and have him open your ass with fingers or small toys before he even attempts to put his cock in there.

As for positions, if missionary isn’t working for you, trust your instincts. Maybe you should get on top, so you can control the depth of penetration, the speed, and you can move your body to get the best angle. Or you could try doggie style, but make sure he doesn’t thrust all the way inside on the first time around.

I cannot recommend any of the de-sensitizing lubricants that are available. Numbing your ass just isn’t a good idea. If you can’t feel anything, you cannot listen to your body’s warning signs that things are going too fast, and you’ll most likely end up with a sore butt the next day. Plus, if it’s numb, you can’t feel all the pleasurable sensations that anal sex can give you, and trust me, you want to feel those.