Having Sex With a Transsexual Woman:
How to Make Love With the Transsexual Female.
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
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.
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.
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.
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
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
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
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,
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?
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.
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
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
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
Did she say she doesn't
want you touching it? Then don't and do something else, instead.
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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.
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
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.
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.
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.
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.
3. Your STD/HIV test results document, if any.
5. An adventuresome spirit.
You can put most of
that in a small "shaving kit." Put the adventuresome spirit
between your ears.
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.
and good luck!
Copyright 2009, by
the author, all publication rights reserved.
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The topic of this
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