Trans SEXUALITY: Anal Sex

By Michael M. Hernandez

So you think you might be gay? What gives? You've always been into women in the past. Now, X number of months into transition, out of the blue you begin to fantasize about other men. That's perfectly "normal". Exploration of our sexuality is what part of this journey is about. It isn't something that everyone does or that everyone needs to do. It's an option. That's the beauty of the transmen's community. Each of us is different.

Fantasizing about men or exploring those fantasies does not make you gay. Also, pleased don't fall into trap of thinking that you are limited to having only one type of sex or that the sexual activity in which you engage determines your sexual preference. Anal sex is just that, anal sex. It happens to be one of the orifices which we all have. But what if you have never had anal sex before?

We are taught a number of things about our bodies particularly the anus, that might present certain obstacles. We are told that they are dirty. That they have one purpose, to excrete waste product. For some guys, their assholes are a source of shame or embarrassment (you know who you are). The only way to get over this is to explore on your own before getting a partner into the mix. We have enough body image issues to overcome as transmen without adding to them by worrying about virginal states. You too can make friends with your butthole and have a good time doing it!

DOUCHING: A New Concept

Some of us were taught that douching meant using vinegar or some other substance and water to clean out the vagina. Mmm, guess again. Douching in the gay male community refers to enemas or "cleaning out" as the process is sometimes called.

Douching is recommended for a variety of reasons. Fecal matter is abrasive increasing the friction that accompanies penetrative sex. Cleaning out will help your sphincter relax making penetration easier, more comfortable, and actually quite pleasurable. It will also ensure that clean-up after sex will entail throwing away the condom(s), glove(s), and chux, washing the toy(s), and little else.

Douching for the first time can be an interesting experience. Initially you might feel a little bit of a chill or a warmish flash. Any new experience takes a little getting used to. What is awkward at first will quite pleasurable as you become comfortable with the process. If done properly, it's not an unpleasant sensation. If done too quickly, it can be downright uncomfortable. The trick is to take your time and to separate the actual physical sensations from their psychological components. In other words, you may have to work at undoing some of the negative programming that most of us were taught as children. Anal Pleasure & Health: A Guide for Men and Women by Jack Morin, Ph.D. (San Francisco: Down There Press, 1999) is an excellent book and will help you to overcome some of these issues.

First thing first. You will need to buy some equipment. It's not as expensive as it sounds. You can purchase a bulb syringe, a enema kit , or a shower attachment known as a shower diverter. These products, with the exception of the diverter, are usually sold either near the feminine hygiene products or the laxatives.


Bulb Syringe: Approx cost $10 - $12

This is simply a plastic nozzle (also referred to as a syringe) which screws into a rubber bulb. The bulb holds approximately 8 ounces of fluid. It is made of harder rubber than feminine douche products and the nozzle is curved rather than straight. The travel douche for me is more of an emergency device for situations where I don't know whether sex is in the cards (and assuming that I'm the one who will be penetrated). It is small and easily contained to ensure privacy, but is not as thorough as the Kit. It can be purchased at any Walgreens, Woolworths, Longs, Savon or other name drug store.

Enema/Hot Water Bottle Kit: Approx cost $15

The kit is comprised of a hot water bag, rubber tubing, and a hard plastic nozzle that gets pushed into the rubber tube. Some kits are sold as enema kits and some include the hot water bottle components. Each tend to hold between 1 - 2 quarts of water. This item can be purchased at the same type of stores as the bulb syringe. While also mobile and capable of travel it does not fit as nicely into a shaving kit. However, it remains highly portable and the best choice.

Shower Diverters: Approx cost $60+

This item is aluminum and is commonly referred to as a "silver bullet" or shower bidet. It includes a "T" shaped joint which has the diverter on it, a long aluminum hose, and a metal nozzle with four small holes for the water to come out. You will need to unscrew your shower head to screw the top end of the "T" into the pipe. Plumbers tape works wonders to make a seal that does not fuse the materials together. The shower head then screws into the other bottom of the "T". The long hose screws into the side of the "T" and the nozzle connects to the hose. The diverter switch is located on the other side of the "T". Depending on which position you place it at, it will either allow water to flow through the shower head or through the hose.

Shower diverters can be purchased at most erotica stores or online. Any erotica store in a gay area of town will tend to carry the diverters. You can also search for products online. Mercury Male Order in San Francisco has this item available in their catalog.

Other Products:

While there are a number of commercial available products, you don't need them. They tend to be for one-time use and can get expensive. Many of these products, such as a Fleet's enema, contain chemicals and other stuff that will make your first experience a bad one. The goal isn't just to be empty, but to have a fun time doing it.

How To Use It

Now that you know what you can buy, let's discuss the use of these items. Chances are that if you own the shower diverter you already know what to do, so I for now let's focus on the other two items.

You may be a little nervous the first time. Don't worry. Make sure that the bathroom is warm then do something to make you relax. Watch a porno movie to get you in the mood. Masturbate so that you are excited, but don't orgasm, at least not yet. Listen to some mellow music. Meditate. Do whatever it is that you normally do. When you are ready move to the bathroom and get naked, if you aren't already.

You will need to fill either the bulb or the bag with fluid. Start with warm water. DO NOT add alcohol to the douche. Rectal tissue is full of capillaries and allows direct absorption of alcohol or other substances into the blood stream almost immediately. The oral ingestion of alcohol requires the stomach to utilize digestive juices to absorb alcohol into the blood stream. If you ingest too much too fast or if your blood alcohol level rises to toxic or dangerous levels you simply puke and in that fashion the body is able to stabilize itself. There is no similar safety device for anal absorption. DO NOT use ice water as it can lower your core temperature and cause hypothermia. Please use common sense. There are things which can be added to the water in moderation. That will be the topic of a future article.

Use your wrist to gauge the temperature of the water. Rectal tissue is more sensitive than the surface of your skin. Everyone is different. A little bit of practice will help you gauge what feels good for you.

Use vaseline or another similar product to lubricate the end of the nozzle. Also lubricate your anus outside and in. Penetrate yourself with a finger to get used to how this feels. Don't tighten up. The more relaxed you are the better this is going to feel. If you are panicked or worried take a deep breath and when you are ready let it out as you commence insertion.

With the bulb syringe you will want to squeeze it until a little water comes out, then insert it. This way you won't be inserting air into your body. While a bit if air will not pose a health hazard it does increase the possibility of cramps. Take the syringe out of your body before releasing the bulb to avoid any water from flowing back into the bulb.

With the enema bag you want to open the plastic flow control clamp located on the tubing to allow water to start to flow a little, then clamp it off. Insert the nozzle slowly until it is inside you. You don't have to place the full length of the nozzle in your body just enough to allow the water to enter your colon. Allow the water to enter your body as slowly or as quickly as you feel comfortable. Try not to rush it. A very fast intake of water is going to create a cramp similar to those that accompany a bad case of the flu. When you start feeling full or a cramp setting in, remove the nozzle. If using the bag you will need to clamp it off before removing it. You do not have to empty the entire bag into your colon before releasing it. That's something that will take practice assuming that you even want to do that.

Get out of the shower or tub and sit on the toilet. Hold the water for a moment and then release it. Fecal matter will accompany the release of the water. Don't bear down or force anything. Your body will naturally expel all of the liquid. Repeat approximately 2 - 3 times until the water that is released is either clear or free from solid substances.

That's basically it. Please note that for health reasons, nozzles should not be shared. You should each have your own.

Butthole Surfing

Now that you are clean you are ready for some action. There are literally a ton of toys available for self play such as dildos, chrome eggs, anal beads, etc., etc. Some people have a tendency to get excited and throw common sense to the wind, Don't become an emergency room statistic. You can do this by purchasing products that are designed for anal insertion. Avoid dildos that have wire in them. I know that common household products are tempting, but do you really want to have to explain what the light bulb, soda bottle, barbie doll, vegetables or other items you might find around the house are doing stuck inside you. I'm not kidding here!! More than one story has been told by ER technicians about what people have done.

If you have ever let your eyes dictate the size of your stomach you will have noted that more often than not there is food left over on your plate. You don't want to make the same mistake the first time out. Ideally penetration would be accomplished with a close and intimate friend who has done it before and can help you through the experience. However, this is not always possible.

If you wind up doing it yourself, a good first choice would be a small butt plug (i.e. short in length and small in diameter). This will free up your hands for other things. You may feel a slight chill or cramp coming on the first time your sphincter relaxes enough for the dildo or but plug to get in. This is normal. Your body isn't quite used to having things travel in the opposite direction. Take a few deep breaths and let the toy slowly slide out of you.

If, for any reason, penetration feels painful in any way, stop. If what you are feeling is mild discomfort, pull out slightly and masturbate. You would be amazed at how quickly discomfort can turn to pleasure. Whatever you do don't force it. There is always tomorrow. It is possible that you didn't use enough lubricant or that one of your newly grown hairs has been pulled into you along with the toy. If you are furry, as I am, you may need to shave or trim your butt hairs a wee bit. The racing stripe may be a little interesting to explain, but it's better than getting abraded. Be careful not to nick yourself. Don't feel that you have failed if you don't manage penetration the first time out. What is important is that you get comfortable with the process and that you learn what feels good to your body. Try again when you are ready. Once it's in and feels good it's time to work towards an orgasm.

Pay attention to where the item was when it started feeling good. As you become accustomed to penetration you will note that your sphincter will become more and more resilient. Voila! That's all there is to it. You might realize that it isn't for you, but more than likely you will discover that anal sex can be quite fantastic!

Surf's up!

Copyright © October 15, 1995
By Michael M. Hernandez
All Rights Reserved


Please send questions, suggestions, topics or requests for further information to