Sex with a transsexual woman is a literal minefield in a number of ways. In this article, I am going to speak frankly to men about making love with the transsexual female. Why a sex article? This site is about trans women and relationships with men. In most relationships, sex plays a major role.

This information has been gathered from many sources. I have solicited comment from many on the various aspects of sex with the transsexual woman, and of course have drawn from my own experience as well. THIS ARTICLE IS SEXUALLY EXPLICIT! If you don't wish to read such material, hit your browser's back button now. Also, sexual slang is liberally used in this article. After all, it's written to educate and inform the average guy, not university professors, so be ready for it.

I'm not going to discuss how to initially seduce a TS or entice one into having sex. We're making the assumption that both have already decided to yank off their clothes while dashing madly to the bedroom. And so here we go.

Topping the man.

Let's dispel one myth right away. Transsexuals are women. Women are generally not the aggressors in bed. Women want to be "taken," they usually aren't the ones to initiate sex by pulling their men into the bedroom. There's plenty of anecdotal evidence to support this notion. Check out the covers of romance novels in any bookstore, for example. Look into a woman's eyes -- notice how they draw you in?

If you're a "bottom" male hoping that a pre-op or non-op transsexual will bend you over and fuck you, well you can forget about it. Women, transsexual or otherwise, generally do not want to fuck you. They want you to fuck them. As a TS lady friend expressed it to me recently, "Women receive, they do not project."

For the guy looking to be "topped," expect to have to pay an escort for that service. That is mostly what they specialize in. If paying for a romp in bed isn't your style, it is very doubtful you will find it anywhere else in the TS community. Cross dressers, however, are a different matter. These are not women, they are men enjoying a dress-up fetishistic fantasy. You may find what you want with one of them.

Initial thoughts she's having.

If this is her first time making love as a woman, she's probably terrified. If she's pre-op, she's worried that you might want to play with that yucky male appendage that she hasn't yet converted into a vagina. She may not want you to touch it at all. If she responds with an erection, she may be very embarrassed, and also very conflicted. How many women want to respond like a male? Not many. If she's like most pre-ops, she would prefer that you pretend it doesn't exist.

She's done the orifice inventory. She knows you want more than just a hand job. If she's never put her mouth on a man's organ before, she's no doubt wondering what that will feel and taste like, whether she will gag (or worse), and she's hoping that you're very clean. Dude, if you haven't showered in a couple days, get it done immediately. And make sure you're squeaky clean before every sexual encounter. And clip your nails, too.

Is she newly post-op or new to vaginal intercourse? She may be concerned about how tight she is. It takes time and experience for that vaginal opening and canal to loosen up. She may be concerned that she's so tight that it will be painful for you. If you have a very long or thick penis, she may be worried about being able to take you at all.

If she's new at giving blowjobs, she's probably hoping she won't appear incompetent at it, bite you, or inadvertently snag your shaft on a tooth. If she's never been butt fucked before, she no doubt wonders how painful it will be.

She's probably wondering if you've passed a recent test for sexually transmitted diseases, including but not limited to HIV. Not tested? Go get it done and hang on to any documentation provided by the testing center.

She's probably wondering whether you will be willing to practice safe sex. If for no other reason than to help her relax, be prepared to do so. She does not want to ruin the mood by having to argue with you about it, and she certainly doesn't want to risk catching a serious disease.

In short, the TS new to sex as a woman may very well be worried or frightened. Don't be surprised.

Bisexual men and the transsexual woman.

I believe the majority of men interested in TS's are bi to some degree. Heterosexual transwomen generally want what GG's want: A straight man, a guy who appreciates them for who they are, not for their genitals. TS's typically don't want to be involved with bi guys. They often cite a few reasons for this:

1. Bi men are attracted to the penis, an appendage they would love to convert into a vagina.
2. Common statement: "He's not attracted to me, he's only attracted to my penis. He only wants a chick with a dick."
3. She wonders if he will still be interested in her once she's had sexual reassignment surgery to convert that penis into a vagina.
4. They are concerned that a bi guy will be sneaking around on her to meet with men.
5. They are concerned that bisexual guys are more likely to contract STD's and HIV.

As with most issues, there is more than one side to a story. The fact that a transwoman was born male is usually a huge drawback for the strictly heterosexual man. Most straight men (but some are open minded) find the idea of intimacy (sex, kissing) with either a pre- or post-op transsexual to be very unappetizing. Therefore, most transsexuals do not meet many straight men that are prospects for a relationship.

As in the section above where some men pursue an unrealistic desire to find a sexually aggressive transsexual to "top" them, many hetero TS's similarly pursue strictly straight men. They are seemingly unaware of how most of these men regard the prospect dating a girl who was born male, but nevertheless they still hope to fulfill the desire – shared with millions of GG's -- for a straight man. The evidence says this is a difficult path.

I'm speaking to the ladies here: The TS who keeps her transsexuality secret until significantly into a new relationship with a strictly heterosexual man is at high risk of being verbally abused and immediately dumped when that heterosexual man discovers the truth. She is also at high risk of physical assault.

Let's look at each of the points above from a bi guy's perspective.

1. A male who has had at least some sexual experience with other men is not homophobic. He can handle the fact that you used to be male. Bi guys are not gay guys. Gay men have no sexual interest in women of any sort.
2. Common statement by GG's: "He doesn't want me, he just wants the pussy." The point is, whether he's bi or straight, if all he wants is your genitals, it's not cool. But it is cool if he wants both you and your genitals, no matter what sort they are at the moment.
3. An actual bisexual male is sexually attracted to both genders. If he's romantically interested in you as well, he will probably continue to be so after SRS. After all, he can "go both ways." And the emotional connection is the anchor.
4. Although filmmaker Woody Allen is quoted as saying, "Bisexuality immediately doubles your chances for a date on Saturday night," it doesn't mean that a bisexual man will be any sluttier than any other man. Don't believe everything you see on the Jerry Springer Zoo…I mean, Show.
5. There are lots of monogamous gay guys, lots of monogamous bi guys and lots of monogamous straight guys. Whether someone is monogamous has less to do with sexual orientation than the nature of the individual you're involved with. A monogamous bi partner will not be any more likely to bring home a disease than a monogamous straight partner.

Do you know of a marriage where a bisexual woman is monogamous with her husband? For how long have you been searching for a man who can accept the fact you were once male?

Heavy petting.

This is usually defined as serious foreplay: Stroking her breasts, butt, genital area, and so on. This is one of the minefields mentioned in the opening paragraph. If she's pre-op or non-op and this is your first time playing around with her, it's best to not give any attention to her penis. Why? Because you don't know how she will react.

But if you know for a fact that she's cool with you touching it -- and you're also OK with it -- then go ahead.

Is she post-op? Stroking her vaginal lips won't release lubricating fluids as with a genetic female, but you can always apply some saliva your fingers to make them slide wetly along the plane of that pussy. Pay attention to her clitoral area. In most cases, as with genetic females, it's an extremely sensitive spot.

If you plan to insert your fingers, use an actual sexual lubricant. K-Y Jelly is a well-known product available in most grocery and drug stores. Adult stores can provide you with various high-quality lubricants. If you think your upcoming date might get this hot, hey pick some up and carry it with you. You can buy them in small bottles.

"The conversation" with a pre-op TS.

There's something you need to discuss with your lady before it goes any further. It's about that dick.

Are you a straight man having your first sexual encounter with a pre-op TS? She probably expects that you won't show any interest at all in that dick. If you feel the same way, great, and it would be useful to say so. Then just ignore it and move on. If you find that you can't get aroused because of the sight of that dick, end the session. Either get to know her better to lower your anxiety level, or say this isn't for you and terminate the relationship.

Are you a man very much into pleasing your female partner with cunnilingus but are staring at a penis instead? You could be pretty much straight or very bisexual, but if you haven't yet bolted for the exit, congratulations. It's time to be forthright and honest with her.

You might explain that orally pleasing your partner is important to you, and you're OK with touching, stroking or sucking her dick (whether or not it's your preferred thing to do), but you don't want to embarrass her or make her angry. Let her know that all you want to do is give her great pleasure. If she's capable of experiencing that with her penis and is cool with you touching, stroking or sucking it, go ahead.

And ladies, it would be an error to assume that if he's willing to touch or go down on you that he's done it before, so don't assume that he's bisexual simply because of that. Do remember that even gay men had first-time encounters.

If you've never sucked a dick before, you might want to ask her to give you feedback on how you're doing. And if you're suddenly feeling nauseated for engaging in what your family and all your friends would label a very homosexual act, for God's sake find the bathroom in a big hurry and kneel before the porcelain throne.

Did she say she doesn't want you touching it? Then don't and do something else, instead.
Oral sex: Her going down on you.

There's an old joke that goes, "There's no such thing as a bad blowjob." That's not true, but if it's apparent that she needs some guidance, turn it into a teachable moment. What matters with a blowjob isn't the level of expertise, it's the willingness to learn. Be patient, tell her what you want, tell her when it feels good, and offer encouragement. Put on a little show when she does something perfectly: Rotate your hips and groan loudly.

If she's uncomfortably scraping the shaft or head with her teeth, gently tell her to back off with that. You can also suggest that she fold her lips over her teeth.

When you're approaching orgasm, it would be a good idea to ask if she wants you to cum in her mouth, or on her face, boobs or whatever. It's always a good idea to tell her when you're about to blow your load, so she can be ready for it, obviously.

The pre-op's penis and female hormones.

If your lady has been undergoing hormone replacement therapy (HRT) for some extended time, do be aware that her penis will likely have shrunk in size. Furthermore, it may have lost its ability to become erect. That doesn't mean, however, that it's lost its sensitivity. After all, part of that male organ will be converted into a clitoris during SRS.

The hormones will also promote breast growth and sensitivity. A high percentage of TS's will opt for implants as natural breast growth can take a very long time. Usually, a TS on HRT will find her breasts to be about as sensitive as the typical genetic woman's.

The transsexual female on HRT will also experience a change in skin texture and will usually also form feminine curves about the hips and ass.

The post-op's vagina and female hormones.

Female hormones can give the post-op transsexual a delightful advantage over the male. Oftentimes, she can achieve multiple, intense, ongoing orgasms.

If she had the surgery only recently, she may not yet be orgasmic. It takes time, often several months, for the nerves to reconnect following surgery in order to produce an orgasm. In my experience with my ex-girlfriend, she became orgasmic within a few months following surgery. But it took well over a year before she became explosively multi-orgasmic.

The artificial vagina does not have the secretion glands necessary to self-lubricate. Intercourse will invariably require a quality lubricant. If there exists the possibility of intercourse (anal or vaginal) on a date, make sure you have some lubricant handy, and at least one condom.

The vagina is surgically fashioned out of the penis. If you are one of those guys who finds the idea of touching a dick with your mouth completely revolting but you love to eat pussy, there will come a moment when it dawns upon you as to where the skin to make a vagina came from. If you have a problem with that, it would be a good idea to avoid going down on her.

The typical vaginal depth ranges between five and six inches. The vaginal walls will not be as flexible as those of a genetic girl. Post surgery, the transsexual is provided with stents. These resemble dildoes only they are rigid, clear plastic. They are not used for sexual stimulation. The surgeon will instruct her to use them daily for several months, starting with the small one, and gradually moving up to the largest one. The stents are used to maintain depth and prevent vaginal wall collapse.

The depth and diameter will be sufficient to accommodate most men, but some guys fall outside the norm. If you're one of those dudes who needs to undress in the dark (else the lady will run screaming from the bedroom), she may not be able to accommodate you, no matter how much lubricant you use. If you insist upon fucking, expect to do anal if vaginal doesn't work.

Some women refer to "fuck-me" heels as "earrings." This is because in the missionary position, when a guy pushes her thighs in toward her chest, her heels get fairly close to her ears. Due to skeletal and musculature differences, it is easier for a GG to accommodate her legs being pushed back so far than it will be for the average TS.

Anal sex.

A certain TS lady friend wrote me: "Anal sex is my favorite.... When a man is in me...I can't get enough. Feeling his taut penis stretch me, then throbbing with a glowing wet orgasm is like a gourmet meal. It makes me feel so warm, cared for, and safe."

It's a good idea for the lady to hit the bathroom first and also douche, to assure that the lower colon is empty and clean.

Use a quality lubricant. Make sure the head and shaft are well lubricated. Even if you're using a lubricated condom, add more lube to the outside surface.

Penetrate slowly. Let her sphincter muscle open and get accustomed to the size of your penis. Push until the head has opened her ass hole and then stop. Give her a minute or two to get accustomed to its size.

Begin fucking slowly then increase the tempo as appropriate.

An uncircumcised ("uncut") cock is a potential advantage in unprotected anal sex. A good part of the back-and-forth movement will occur within the sheath, not against her opening, thus reducing wear and tear.

What to take on a hot date.

1. Condoms.
2. Lubricant.
3. Your STD/HIV test results document, if any.
4. Mouthwash.
5. An adventuresome spirit.

You can put most of that in a small "shaving kit." Put the adventuresome spirit between your ears.

Seduction and teasing.

Why is this portion at the end rather than the beginning? Because by now you know what you can and can't do, what turns her on and what turns her off. Sex is an integral and wonderful part of most relationships, and if you're like me, you'll find opportunities to do hot little things to arouse her.

Write a very explicit note on a little piece of paper and tell her to put it in her bra and keep it there all day long. Believe me, because she can feel that note against her boob, she will be thinking about it (and your intentions) constantly for hours.

Or, maybe you're at a party. Maybe you're on a hike. Or in a dark movie theater. There are ways to tease her in such locations.

Perhaps you're in a big box home store looking in the lighting aisle. Get face to face with her, drape your arms over her shoulders and pull her close. Kiss her lightly on the neck then kiss her tenderly on the lips.

Should the others in the lighting aisle wander out of sight, run your fingers over her breasts and fondle them through the fabric. Lightly tweak her nipples. Run one hand down to her crotch and stroke to stimulate for a moment, regardless of what sort of genitals she has. See if you can get her to moan and her knees to buckle. Kiss her again and fondle her ass.

Then playfully swat that ass and say (as though it's her fault), "Come on, quit distracting me. We gotta choose a fucking floor lamp."

She might attack you when you get back to the car (keep an eye out for mall security). Or maybe she will wait until you get home and the garage door closes before attacking you. These are the sorts of attacks that men enjoy.

Have fun and good luck!