A: First off, pretty much anything you see in porno is an exaggerated sex practice. The performers are taking certain risks, which they understand going in to the scenes. Porn performers are required to know and be able to prove their STD status at all times.

To answer the broader question we can give you some information about cleanliness and risks of anal sex and ass to mouth play of any kind (ass to mouth and rimming).

Cleanliness – To prepare the rectum and anus for sex people usually take a shower or bath, and use an enema. There are 2 basic types of enema. One is the larger enema bottle that comes with a hose. A person lies down in the bathtub and receives some water into their rectum. Then they get up and let the water out into the toilet. The other method is to use a small squirt bottle called an “anal douche” or “disposable enema” from the drug store. Dump out the liquid that comes with the anal douche and replace it with warm water. The water can be squirted into the rectum while the person sits on the toilet and lets the water out into the toilet. The process can be repeated a couple times. With any enema it’s important to wait 15-20 minutes after before having sex so the rectum can recover.

Risks – Even with enemas there are still several health risks to condomless anal sex and ass to mouth. One risk is STDs. It’s possible to transmit HIV, Herpes, HPV, Syphilis, Chlamydia, and Gonorrhea between a penis and a butt. Using a lot of lube reduces the risks of some of these STD transfers by a significant amount. Even if you aren’t using condoms, use a lot of lube.

The risks of any contact between a person’s mouth and something that’s been in an ass (or is an ass) are Hepatitis and bacterial infections. The risk there is that some fecal matter gets into the rimmer’s mouth. No amount of douching can remove this risk. The good news is that Hepatitis can be tested for and also there is a vaccine.

If you are into this sort of play we suggest you consider using condoms and dental dams, get yourself and partners tested for the STDs, and also consider getting the Hepatitis vaccine.

A: First off, it’s perfectly ok not to reach orgasm from oral sex. It doesn’t mean that you or your girlfriend have anything wrong with you. It probably just means that you’re stressing yourself out about how you will perform (meaning, orgasm). If your sex life is satisfying as it is, this isn’t something you have to ‘correct’.

That said, it sounds like it’s causing you some worry, so let’s look further. Regarding masturbation: It’s a lot easier to orgasm from your own touch than it is from someone (anyone) else’s, simply because you can immediately feel what’s working and what’s not, and adjust for it accordingly. Also, there’s a lot less pressure to perform when you’re on your own, of course.

About your erections coming and going during your intercourse: It’s not unusual for have highs and lulls during intercourse, but those too may be linked to your anxiety about performance and satisfaction with your girlfriend. Or it could be, as it happens with a good number of couples, you have fallen into a routine and it becomes less exciting. One thing you can try is to experiment a bit with your sexual activities and try other things. The newness can sometimes lead to new arousal.

If it’s a matter of experience, both of you might take a look at some good books about sex. One very good one is “The Good Vibrations Guide to Sex”, which has a lot of helpful hints and techniques, or “The Ultimate Guide to Fellatio” by Violet Blue. Both books are available at bookstores or at amazon.com

Lastly, if there are particular things she does that feel bad, or tend to make you loose your erection, you may want to try giving her some gentle guidance, that can help as well. (Something along the lines of, “This thing you do feels really good. Do more of that.” tends to work very well.)

So here’s the problem: I’m fine experience-wise with my own pleasure because of, you know, owning a vagina that’s at my disposal to experiment with, but I’m not sure of how to go about really basic manual and oral sex on the male side. My boyfriend is comfortable with (and very skilled at) giving both manual and oral stimulation, and I feel badly not properly reciprocating. I’ve given a couple hand jobs, but I feel uneasy about it, and not sure if I’m “doing it right,” which is one of those awkward questions I’d rather not ask my boyfriend while I’m trying to give him an orgasm. I haven’t attempted oral yet, and the thought of it makes me pretty nervous. I know people’s experiences differ, and that I’m just going to have to live and learn at some point, but I’d like some advice on how to go about things, especially on the oral side, and hopefully come close to giving as much as I’m getting.

A: The best advice we could give you on how to please your boyfriend is to ask him. Seriously, even really experienced people need to ask their partners what they like because every person is different. So as you are doing things, ask him questions like, “is this good?” “should I go harder?” “do you want it faster?” etc. Also, it could be that your partner likes answering your questions. It can be really hot for some people to get to “show you the ropes” and teach you the way they like things. Think about it- would you mind answering questions about how you like to be pleasured? Probably not, if it means your boyfriend is better at pleasing you!

That being said, we do have some general information on what many guys like for oral sex. First, be careful with your teeth- try not to scrape or bite him. Second, the head, specifically the underside of the penis towards the top, is the most sensitive part. Many guys like to have this area licked, massaged, or played with. For some, however, this part will be too sensitive, and too much stimulation could irritate your partner- which is why you have to ask him.

Another tip for oral sex is to not try to put his entire penis into your mouth. It probably won’t fit, and you’ll probably just end up choking on it (not so sexy). So use your lips, tongue, mouth to lick and suck a little along the sides or around the top and use your hands to stroke his shaft where your mouth is not.

For hand jobs, the general idea is just to stroke his penis, much like he would if he were masturbating. The best way for you to learn how to do this is probably to have him masturbate in front of you (try asking him to touch himself for you), then try to duplicate what he does. In general, though, you want to stroke him up and down, slowly at first then faster as he gets more turned on. Lube can be really helpful with hand jobs because less friction = more pleasure. Ask him if he wants it harder or softer, faster or slower.

You can also try playing with his balls, either by licking them or gently rubbing them with your fingers, either as part of a blow job or a hand job.

You might also try looking at Very Koi, which has some tutorials for masturbation and oral sex. It might have some ideas or tricks you could try.

It’s not fair. It is so easy for him to cum and he gets to do it so often. It is hard not to feel some resentment towards him even though he really does try. He says he enjoys eating me out, and I believe him, but sometimes he is just not good at it. It doesn’t feel like he is in sync with me or my needs. We have talked about it quite a bit, and I even bought a book for him and underlined stuff that I agreed with or found helpful.

It is hard to talk about it thought. I try to communicate what i want, but in the heat of the moment it feels impossible to find words to describe what I need. When I do find the words, he seems to either just not get it, or he does exactly what I say to such extremes that it ends up not feeling good because you can’t just do the one thing to get me off. And then he gets frustrated because he is doing what I say and it still isn’t working.

A: It sounds like you have tried several of the things that we recommend when we hear this problem, but I will reiterate that communication is key to any successful sexual relationship. It might be helpful to talk him through the whole experience of oral sex. Or you could try to introduce a vibrator into your sex life. One thing to ask is whether you have ever enjoyed oral sex as much as you might want to with any other partner? If not, maybe oral sex is just not something that you are really into and you could try other types of stimulation to reach orgasm. Also, have you tried masturbating to see what you really enjoy and what you don’t? If you are comfortable with it, you could let your boyfriend watch you while you pleasure yourself so that he can see what your technique is and try to apply that the next time he gives you oral sex. Sometimes when you try to force an orgasm to happen, it can make it that much harder to actually cum, so try to relax and enjoy the ride, so to speak. If things get frustrating, it might be helpful to take a break and come back to it later.

Here are some websites that you and your boyfriend can refer to:
sexuality.org
sexhealthguru.com

There is are also video guides that you could try. We found one called:
“Nina Hartley’s Guide to Better Cunnilingus”

Also, here are some books that I can suggest if you would like more information:
“She Comes First” by Ian Kerner
“The Ultimate Guide to Cunnilingus” by Violet Blue
“Box Lunch: The Layperson’s Guide to Cunnilingus” by Diana Cage

What could this be? I know she wouldn’t taste anything if I ejaculated way down the throat. But given the sensations that I felt I think something might have happened differently. I think it was an inward or non-ejaculatory orgasm. Could it be?

A: Thank you for your question. There are several possible explanations for your experience. It is possible that you experienced a full body orgasm without ejaculation. Often men who report having full body orgasm state that they are still full of erotic desire and are able to continue their sexual activity. Some men work hard to learn how to experience a full body orgasm without ejaculation. So is that is what happen to you consider yourself gifted.

It also possible that you had a retrograde ejaculation. Retrograde ejaculation occurs when semen enters the bladder instead of emerging through the penis during orgasm. Although you still reach sexual climax, you may ejaculate very little or no semen. This is called a dry orgasm. Retrograde ejaculation isn’t harmful, but it can cause male infertility.

Retrograde ejaculation can be caused by medications, such as high blood pressure or mood disorder medications, health conditions, such as diabetes, or surgeries that affect the nerves or muscles that control the bladder opening. If retrograde ejaculation is caused by a drug you’re taking, stopping the drug may be an effective treatment. For retrograde ejaculation due to a health condition or as a result of surgery, treatment with drugs may restore normal ejaculation and fertility. But treatment for retrograde ejaculation is generally only needed to restore fertility. Some men experience retrograde ejaculations only once in awhile most of their ejaculations emerge through the penis.

It is also possible that your girlfriend did not notice or taste your ejaculation due to something she ate or drank prior that had desensitize her mouth, or it was in her throat as you suggested

A: As with both men and women, pre-ejaculation can not affect your health. For men, pre-ejaculate fluid is usually released before the male reaches orgasm, which results in the ejaculation of semen. Pre-ejaculated fluid prepares the urethra for the semen and helps in lubrication during sexual intercourse.

Your wife may not like to give oral sex because of taste of the pre-ejaculate and she may not be comfortable in the act of oral sex. If that is the case you should have a dialog on her hesitation to suck your penis and maybe suggest that you both read some books on the topic and/or visit websites. Also, there are flavored oils and creams that your wife can put on your penis that can somewhat dilute the taste of the pre-ejaculation.

A: First times can be a lot of pressure and stress. For most men having one orgasm by masturbation or oral sex allows them to keep a second erection for a longer period of time. Most men need 10-15 minutes before getting a second erection. Remember, if you do cum once and would like to get another erection there are many activities you can do for and with your partner while you’re waiting to get hard – like oral sex for them or other stimulation.

We recommend that if you know you’re going to have sex in the evening, plan to have an orgasm in the afternoon. That way you’ll be less sensitive for your sexual date and you won’t have to depend on oral sex before intercourse. It will take some of the pressure off.

A: We’re going to assume you aren’t attempting to hide your status as FTM (pre-bottom surgery) from your partner.

You’re on the right track by talking to your partner about it. It’s important to know what aspects of fellatio your partner enjoys and/or misses. Some women enjoy the act of fellatio for the psychological aspect (a perceived power exchange dynamic or for a feeling of servicing their partners), others enjoy it for the visual effect, and others enjoy the tactile sense. If you know what your partner is missing, or why she’s missing it, you may be able to work around those issues with a prosthetic such as a “Pack and Play” style dildo or some other dildo that feels to her like a biological penis. Since you’re planning on doing the bottom surgery you might consider this a temporary measure, or, perhaps in addition to other lovemaking play that the two of you engage in, even after you complete your surgery.

A: We’re going to assume for this question that you are asking about using the mouth to stimulate a partner’s genitals, and not their anus (a.k.a. rimming).

The safety of oral sex depends on whether either partner has a sexually transmitted disease (STD). The risk of HIV transmission is extremely low, but various other STD’s can be transmitted through oral sex. Some STD’s can be transmitted by skin-to-skin contact and others can be transmitted through mucus membranes or fluids, so the mouth and genitals are both areas of concern.

If neither partner has an STD, both giving and receiving oral sex is safe for men and women. A woman cannot get pregnant from giving or receiving oral sex. It’s not harmful to ingest either semen or vaginal fluid. As long as it is comfortable for both partners, oral sex can be a very enjoyable low risk activity.

The San Francisco City Clinic has a handy chart that shows STD risks by activity type.

A: You ask a fine question. It seems that there are several competing theories for the origin of this phrase. The two most convincing explanations we found were the following:

From Ask the Couch:

“This term, now widespread in English-speaking countries, spread from the USA in the 1960s. A puzzling misnomer to many, to blow in this context is probably a euphemism for ejaculate, a usage occasionally recorded in the 1950s. This may itself be influenced by the there she blows of whaling cliche. An alternative and equally plausible derivation of blow job is from the black jazz musicians hip talk expression blow meaning play (an instrument). This term probably caught on in Britain and Australia simply because there was no well-known alternative in existence.(1)”

…and…

From the Maven’s Word of the Day:

“This question has been asked by absolutely everyone I know. And for all the wondering we’ve done about why anyone would give the act of fellatio such a misleading sobriquet, there has been little written about it. There are, however, two well-argued schools of thought.

One explanation ties the phrase to the jazz slang blow meaning ‘to play an instrument’. From there you get the semantic connection of working a tool with some skill, presumably involving the mouth, and there you go.

The second school of thought proposes that the blow in blow job indicates the climax, and is also related to the expression “to blow off steam.” Although the phrase blow job dates only from the 1940s, there is a reference to blowing (someone) off, roughly equivalent to the modern phrase “getting (someone) off,” in David W. Maurer’s 1939 glossary, Prostitutes and Criminal Argots.”

There are many other competing folk etymologies for this phrase, but these at least seemed to ring true to us.