Homosexual transsexuals, HSTS, are as interested in sex as anyone else, and arguably more than most.
There are two sides to this question: sex from the point of view of the HSTS and sex from the point of view of her partner. The author has insufficient knowledge to discuss sex as regards FtM HSTS, although some of the precautionary advice will be relevant. I am indebted to many HSTS whom I know personally and especially my partner, for filling in the details.
Sex for the MtF HSTS.
All MtF HSTS start out with penises but the overwhelming majority wish to be penetrated. This is something of a conundrum, but it is solved by the male anatomy, which gives her both a penis and an organ that can serve as a substitute for a vagina, her anus.
There are a few things to note about anuses. The first is that they are not principally evolved to accept entry, although, as has been pointed out many times, the male ‘g-spot’ is inside the anus, which seems like a curious place for it to be. They are also evolved to remain tightly closed except when the individual wishes to defecate and tend to contract or ‘pucker up’ if stressed. So any attempt at forcible entry is likely to be extremely painful. Perhaps worse, it might provoke a fear reaction that will make it more difficult to enter in this manner in the future, especially if the attempt fails, due to the girl’s reactions either physically — eg by clenching her anus tighter — or emotionally.
It is very easy to damage an anus by being rough and bleeding on first entry is a sure sign of unpreparedness. An erect male member is going to stretch the anus whatever happens, so wisdom suggests a fair bit of preparation first.
This really should begin weeks before sex is attempted, with regular dilations using an object — one that cannot get lost in an awkward place. You will not appreciate a trip to the ER to get it out again. Some recommend a 2-inch paint brush with a well-rounded handle. Dilation should be done while using or imagining sexually stimulating material.
Before you begin, make sure you’re relaxed and at least a little aroused. You might feel a little hesitant to touch your anus, because of fears about hygiene. The best way to overcome this is to begin your exercises sitting on a bidet, in the shower, or better, a warm bath — but not too hot, as there is a risk of fainting.
First you should defecate to remove all material from the colon. Wash the area thoroughly with soap and water. If you have a conventional bidet, then fill it with pleasantly warm water and sit in it while you clean yourself. Use your fingers to remove any material and change the water till it is completely clean.
An ideal instrument is the ‘bidet attachment’ which is a kind of water-jet pistol that is plumbed into the house water supply. It has a trigger which operates the flow of water. The best ones have a rounded shape that will allow you to gently insert them into the opening, then squirt in a jet of water. Express this over the toilet bowl to remove any residual matter.
Be aware, however, that if you live in the temperate zone and the device is plumbed into the cold water supply, as it should be to avoid scalding, then the water may come out close to freezing in winter! This is not pleasant.
In that case, use an enema bottle or douche to inject warm water and clean the area, Do NOT use soap internally as not only is this irritant, it will break down the natural and protective mucous that lies on the skin inside.
Once you are happy that you’re clean inside, you can move to a bed or couch if you like. You can put down a towel to catch any excess lube. Apply a water-based lubricant like KY jelly to your anus. Most of these are based on glycerine as a safe lubricant. In solo play you can use a mild non-irritant oil, but remember that oil will destroy condoms so it is better to get used to the water-based ones.
Now you can relax and open your anus with gentle insertions of a finger. Trim your nails first! Masturbate at the same time if you find this pleasant. Once the anus is relaxed, try to insert a dildo of some kind. This first one should be narrow, about the thickness of a finger, but with a broad base so that can’t slip right inside. Explore yourself internally and try to understand what the sensations you are feeling mean.
Over the course of a couple of weeks, depending on how relaxed you are, you can move up, preferably in stages, to a dildo about 2cm in diameter or slightly more. The bigger you want to use, the longer it will take to get there, but day by day your anal muscles will stretch and relax. In fact, most of the resistance is psychological and, as long as no force is used, no harm will be done. Some discomfort is normal at first but if you feel real pain, stop and relax. Leave it till the next day.
Sex with a partner
Now, let’s imagine you are ready to try this with a partner. There are a few other things you have to consider here.
First, make sure you really trust the man. This is crucial. It will help if he has experience with girls like you. Next, you must realise that, in receptive anal sex, the risk of contracting a Sexually Transmitted Disease (STD) from your partner, as person being penetrated, is much higher than for a woman. This is because the mucous membrane of the colon is delicate and, while it will grow stronger through time, it will tend to ‘micro-tear’. You can’t feel these, because there are no nerve endings in the mucous membrane; most of the sensations you’ll feel — which are powerful — come from stimulating nerves in the surrounding muscles and the prostate. Anyway, there are other things to think about in coitus. But these micro-tears can permit entry of viruses or retroviruses into your bloodstream.
Use a condom
So the rule is: use a condom. Do NOT use two, as this affords lessened protection, since the friction between them can lead to tearing. Use a good, water-based lubricant, preferably the one you’re used to. It might help if you have a drink or two beforehand, but do NOT get drunk. You need to be in control.
Before any sex activity with a partner, clean yourself using the routine you have learned. This will help you relax; it’s by now a familiar experience. Nevertheless you are likely to be both excited and apprehensive. Take things slowly.
Delivering a nasty surprise, in the form of a penis covered in faeces, to your partner is a bad start to a relationship and pretty much guaranteed to ruin the sex session. So clean thoroughly.
Remember that it is inappropriate and possibly even dangerous, for you to have anal sex if you have any form of stomach upset, constipation or diarrhoea. If this is the case then you should use another form of sexual contact, which we’ll get to.
The best position to begin with is to have your partner lie on his back on the bed and then kneel or squat over his penis. This gives you good control over the depth and speed of penetration. On the other hand, in this orientation your anal sphincter is normally tightly shut to prevent anything coming out, so you’ll have to physically open it. You do this by pushing down as if you were trying to defecate. This should present no risk if you have cleaned properly. If necessary, use your hands to separate your buttocks.
Your partner will have to be really hard to enter you, especially if it’s your first time. Give him plenty of visual, oral and manual stimulation. Use adequate lube, but don’t smother the area in it. If you’re too slippery, you might not be able to get your partner’s penis in. The lube should be inside you and on the head and shaft of his penis, not plastered all around your buttock cleft.
The anatomy of the anus has two rings of muscle, called sphincters. The outer one can be opened voluntarily, which you have just done by pushing down. The inner is not under voluntary control but it will relax and open as it feels the head of the penis slide in. Do not rush this. Bounce gently up and down on your partner’s penis until you feel it pass the second ring of muscle then sit down on it and take it all the way in. The sensation, I am assured, will be breathtaking.
The other method, in first encounters anyway, is for you to go on hands and knees on the bed. It is best if the man stands on the floor beside the bed, so that he is not bouncing around on the mattress. Alternatively, you can both be on the floor with him kneeling behind you. This position will make it easy for you to spread in order to take him but you’ll have very little control over the depth or speed of entry, especially if the man is holding you by the hips. He needs to understand that you could experience real pain.
It is not at all uncommon for a girl being anally penetrated to lose the ability to speak. Be aware of this and agree a non-verbal stop signal. Just groaning will likely encourage him. Make it something like slapping the bed or the floor. Again, repeated insistent, but not forcible, thrusts of the penis into the anus will relax it enough to open. However, as the penis fully enters you, you are likely to feel a stab of pain. Try hard not to pull away. If you can, just pause, relax, take a breath and push yourself onto his penis. The pain will quickly pass but if you have to go through the procedure again because you pulled off, then you will feel it again. Better to push on. Try your very hardest to keep relaxed and don’t allow your muscles to contract. Keep open, even if your natural reaction is to squeeze him out.
You will probably feel an almost overwhelming desire to defecate at first. You should have encountered this in your solo rehearsals and learned how to control it. It is the natural reaction to having a large object in your rectum, which the body interprets as a stool ready to exit. It will quickly learn the difference but at first it can be surprising.
Once you have mastered being penetrated, then you can contract your muscles as much as you like — your partner will love it — but for now it will hurt, so don’t.
It can be hard for a man to orgasm with anal sex, especially if you are very tight. I know that sounds paradoxical, but it is the case. But you don’t want him going on for 20 minutes on your first session, though you might later. Do not be fooled by porn; the actresses are experienced!
If he’s inexperienced your partner might not understand that an anus is essentially the other way round from a vagina. While a vagina, including a post-op transwoman’s, is relatively soft and slack at the entrance, it tightens up as one penetrates deeper. This stimulates the glans or head of the penis.
An anus is the precise opposite. It is tight at the entry and then loosens off into a warm, soft canal, deeper in. Some men might need to use shallow penetration in order to maximise stimulation of the glans and allow orgasm. Note that if he’s prone to early ejaculation, he’ll probably be less likely to do so, deeper in.
During your solo play you should have discovered which parts of your insides give you the greatest pleasure, so try to bring yourself to orgasm by stimulating them with his penis. This should not be very difficult, especially if he’s big. If you are on feminising hormones, your orgasm might be completely internal and involve only a tiny amount of penile ejaculation. Many girls achieve orgasm this way without even touching their penises.
Most girls climaxing anally like this report intense sensations, far stronger than they experience with penile stimulation. You will almost certainly experience convulsive muscular contractions, which can be enough to force your partner’s penis out of your anus. You don’t want this to happen as you need to complete your orgasm, so be ready. If you’re on top, put his hands on your hips and get him to hold you on to the penis. If you are kneeling, the same or reach back and grab him.
For some girls, lying face down on the bed is the best solution to this problem as the man can use his weight to keep his penis inside and continue to stimulate your prostate and anus all the way through your climax. This position, however, produces intense sensations and is probably not ideal for a first time. Missionary, with your ankles over his shoulders or your legs spread wide, is also effective. Remember to arch your hips up towards him as you approach climax, to keep his penis deeper inside you.
Once you have climaxed, you might find the presence of the penis still inside you overwhelming. If so, pull off and remove the condom from it. Then either orally or manually stimulate your partner to his orgasm.
A transwoman once explained this to me. ‘Pain,’ she said, ‘Is an essential component of anal sex. It’s like walking a tightrope between pain and overwhelming pleasure.’ But that does not mean that sex should be painful.
Any time a nerve is stimulated in a way that it is unused to, especially in a sensitive area, it can interpret that as painful. Through time, however, with repetition, that interpretation can change to one of pleasure. Think about runners. The first time anyone runs for any distance they may experience discomfort and pain, but as they get used to doing it, their bodies re-interpret these feelings as pleasurable. The same is true of anal sex.
Some girls never overcome their sensation of discomfort and they are probably best advised to consider GRS to give them a neo-vagina. This will allow them to avoid using the anus altogether. Others love the sensations of anal sex so much that they still do it even after GRS — as do women, of course, who have an OEM vagina.
As you can see, anal sex is rarely as spontaneous as vaginal sex can be, even if you are no longer using condoms with your partner, because of the need to clean thoroughly. However, you can get round this by going through your cleaning routine before initiating the sex session. Just quietly excuse yourself while he’s having a drink and then come back and surprise him. Or, if he’s a morning man, slip out of bed to clean yourself while he’s still asleep and wake him up with some fellatio. He’ll appreciate it.
We have always assumed that you will use a condom and you should. However, if you have become close with a man and you trust him and believe he is committed to you, then it is likely that one or other of you would like to try unprotected or ‘bareback’ sex. From the point of view of the man, this feels vastly more pleasurable, as condoms rob most of the sensation even of anal sex, especially in the deeper area.
If you are to do this then you really must get a mutual blood test for STDs. No matter how honest he seems, you need this protection. And you must be able to trust him not to cheat with other girls. Remember that straight men who like transwomen might also like ordinary girls. They might prefer a transwoman for anal sex but a pre-op HSTS can’t offer him vagina. He is a man and he might slip. It is hard to advise how to deal with this but, if you suspect he is likely to cheat, don’t have unprotected sex with him. At the very least, repeat the blood tests regularly. In the porn and sex-work industries this is carried out every month, for very good reasons.
Do not, by the way, assume that because you have had unprotected sex with a man who is HIV+, you are automatically HIV+ too. This is NOT the case. You need to have had blood-to-blood or semen-to-blood contact and even then there are variables, such as your partner’s viral count at the time of the contact, and others, that may affect your risk of infection. If you have conditioned yourself to receive penetration and you have used a good lubricant, there is still a chance that no micro-tears will have occurred. Also bear in mind that the longer his semen is in contact with your delicate mucous membranes, the more chance there is of infection. So douche after sex, if he ejaculates inside you or, better, make him pull out and ejaculate on your body or face.
This is not an encouragement to have unprotected sex; rather it is an injunction to you to PROTECT YOURSELF and not to assume you have been infected, or that the damage has been done, so anything goes. Immediately revert to using a condom and GET TESTED.
Many men, when first confronted with the reality of sex with a pre-operative MtF HSTS, are confused. While an HSTS can be naturally penetrated, the process is not as straightforward as with a woman. In addition, if the girl is inexperienced, then the potential for problems is high.
In order to penetrate, you must either be really hard or she must be already dilated. This can be achieved with a dildo. The anus will naturally ‘open up’ after a couple of minutes’ stimulation and, if she’s willing (and you can wait) then you can use the dildo prior to entry.
Unless she is really slack, which is unusual, however, you’re going to feel tightness in the area of her sphincter muscles or ‘ring’. Beyond that, at first, you might feel very little at first. It’s just because the squeeze on your penis is so tight. As she relaxes and opens up, you’ll become more aware of the sensations around the glans of your penis.
Remember your Kegels
At first, however, especially if she’s really tight, you might actually find the blood that makes your penis erect being squeezed back out by the tightness. To combat this, do your Kegel or pelvic floor exercises regularly and make sure you are properly hard before entering.
As an aside, if you are used to having anal sex with a woman, you are in for a surprise. It is the author’s experience, and that of other men whom he has interviewed, that an HSTS’ anus can be much tighter than a woman’s. Indeed, a famous Roman, (name) on being challenged by his wife for mounting his boy slaves when she had an anus too, is reputed to have said, ‘No, my dear; you have two vaginas.’ The Romans evidently knew a thing o two about this.
As we’ve said above, girls must practise scrupulous anal hygiene before having sex, and you must give her time to do so. Most girls prefer privacy while they are doing this. There is always a level of cognitive dissonance in an HSTS’ attitude towards anal sex and, while she might be delighted to shower with you, this more intimate act of internal cleansing she may wish to do alone. Please let her do so.
Your partner IS A GIRL. She is not a man, despite the presence of a penis. She needs no less gentleness and care than any other girl. If she’s more experienced than you, she’ll be able to set the guidelines — just do as she says.
‘Rimming’ or anilingus, is the matter of orally stimulating your partner’s anus. This is mainly practised on girls by their partners and serves much as cunnilingus does for women: it sexually excites her, relaxes her entry and moistens it.
It is absolutely vital that anyone intending to receive this pleasure should be super-squeaky clean. A properly clean anus will taste and smell of nothing at all. So, dear Western readers, please understand that the almost universal Western practice of wiping the area with tissue is totally inadequate. If you don’t believe me, take some peanut butter, then spread it over the palm of your hand. Wipe it with a dry tissue and then lick it. Still taste peanuts? Enough said.
In addition, sweat accumulates in this area and can result in bacteria establishing, that can produce an unpleasant odour of vinegar. Always use a bactericidal soap in this area. (But never, as above, inside the anus; use only plain water to wash there. The mucous lining of the anus and rectum prevents anything nasty from sticking and ensures that it’s easily flushed out.)
You need to wash the area using a proper bidet, a bidet attachment, or in the shower, as above. Obviously you should do this as part of your regular pre-sex cleaning routine but remember that a passionate kissing session could easily end up with his head between your legs before you have time to ‘excuse yourself’. You do not want him to get an unpleasant surprise, so you need to wash several times a day with soap and water, as well as, obviously, after you defecate.
Few men profess to enjoying receiving anilingus but for those who do, the cleanliness rule is paramount.
The actual practice of anilingus and anal stimulation involves a little more creativity than cunnilingus, since the opening we are about to pleasure is situated in the buttock cleft. There are three easy positions in which to access it. The first and is for the girl to sit on the man’s face. She needs to make sure he can breathe. You can do this as a part of sixty-nine, in which the girl fellates the man while he rims her. Alternatively, she can turn round and face the other way, in which case her scrotum and possibly penis will be on his face and he can enjoy looking up at her body and face as he pleasures her.
Another is for the girl to go on hands and knees, cock her posterior upwards and spread her legs. This should open the buttock cleft enough to permit access. Yet another is to lie the girl on her back and put one or two cushions under her lower back to raise her up. Lift and separate her legs and, placing your hands behind her knees, push them up towards her shoulders. Her entire genitalia will now be exposed for whatever form of pleasuring you mutually enjoy. (Remember that many HSTS are uncomfortable with their penis or scrotum being touched. Be aware of the signals she gives you.)
These last two positions, by the way, have the advantage that the now thoroughly excited, we hope, girl is perfectly positioned for her partner to enter her!
Pre-op HSTS can be divided into two groups: those who like to have their penises sucked and played with and those who do not. Men should find out what their partner’ preference is before touching it. If she doesn’t like it, stay away from it.
Remember: HSTS want straight, not homosexual men and your lover may be testing you. It is not at all uncommon for a girl to ditch a lover for having displayed too much interest in her penis. Ask yourself why you want to play with what is, after all, another male organ. If you’re only interested in that, then perhaps you would be better having sex with another man and accepting your homosexuality. If you’re only doing it because she wants you to, then that’s a different case. But it is relatively rare to find an HSTS who wants to be fellated — or at least, who will admit it.
HSTS do self-lubricate anally, contrary to popular opinion. However, this does not begin until the girl has been thoroughly stimulated by penetration or similar insertion. A good water-based lubricant is always required, although her own natural fluids might supplement this as the coitus proceeds.
A clean anus tastes and smells of absolutely nothing at all. Any unpleasant odours point either to poor anal hygiene prior to sex, or to some gastric issue that must be investigated by a doctor prior to the next session.
Yes, it is absolutely possible for an HSTS to climax using only anal stimulation. This is normal. The popular myth that ‘an anus is not a sex organ so orgasms are impossible’ displays complete ignorance. In fact, the prostate gland, which sits at the base of the penis and is responsible for producing about 90% of ejaculate, is extremely sensitive to massage and stimulating it in the right way will provoke massive orgasms in the individual.
The prostate sits about 3-4 centimetres inside the anal opening itself and anterior (to the front of) to the anal canal itself. It will be felt, by an inserted finger, as a soft bulge that swells and firms as climax approaches. A penis or other object entering the anus at the right angle, slightly angled towards the front of the abdomen, will bump against the prostate, causing intense sensations that can lead to orgasm. If the girl is on HRT, her orgasm may not be accompanied by ejaculation, but it will be by anal and abdominal contractions and even loss of motor control (as if she had just fainted.) It might take her a moment or two to recover.
As well as the prostate, the anal sphincter and the area just inside it, are both extremely sensitive and many girls can bring themselves to orgasm just using the tip of a finger. Practise this and teach yourself how to do it.
Any Registered Nurse would be able to correct the ‘no anal orgasm’ myth, by the way. It’s a canard.
The biggest myth of all:
your HSTS girlfriend wants to fuck you.
NO. This is extremely rare. If you seek to be penetrated, then stay away from HSTS. You can still have a trans girlfriend, but not an HSTS one. Any transwoman who would do this will either be a gay crossdresser or an autogynephilic transvestite. In either case, understand that your desire to be penetrated means you are not straight. You might be bisexual or you might yourself be autogynephilic. But you are not a straight man. HSTS are only interested in relationships with straight men and it would be better if you respected that.
Other ways to have sex
There are always times when anal sex is, for one reason or another, not possible. Indeed, some girls need a day’s rest in between sex sessions, especially if they tend to be wild in bed. Other reasons might include stomach upset or, simply the lack of a condom.
Here are a few other methods to have fun.
If you are not ready to indulge in anal sex, or you are unable to deal with the pain, then you might have to use oral sex, manual stimulation or mutual masturbation. remember though, that if your partner is a straight man, he is going to want to penetrate you sooner or later, and usually sooner. However, since much of the pain you feel is actually psychological, you might well find that other techniques, over time, make anal sex easier.
Oral sex or fellatio
It is harder to acquire STDs via oral sex, in particular HIV, but still eminently possible, so either use a condom or at least make sure he does not ejaculate in your mouth. Every man is different in what gives him pleasure; you listen to the sounds he is making and judge. If he’s big, wrap your hand round the base of his penis and only allow the head to enter. DO NOT try porn-fuelled techniques like ‘deep-throating’ until you really know what you’re doing. For your partner, you vomiting on his belly or having to rush to the toilet making puking noises is about as much fun as pulling out his penis and finding it covered in faeces. Not nice for him and highly embarrassing for you.
Popular amongst some homosexual males, this simply means what it says: the partners masturbate together. An HSTS on feminising hormones is likely to enjoy this much less than anal sex, however. It provokes some cognitive dissonance in the first place, and in the second, she might find her ability to become fully erect is limited (put that another way: she will prefer to orgasm by anal stimulation, which does not require the penis to be erect.) Many HSTS prefer not to have their penises touched.
Frotting or frottage.
‘Frotter’ is French for ‘to rub’ and, as you might guess, this involves the partners rubbing their penises against each other’s bodies. Again, this is popular amongst homosexual men, but will likely be less so for HSTS, for the same reasons as above. Some girls do enjoy it, especially those who have learned to orgasm by rubbing on the bed or a pillow and have difficulty using only their hand.
This was popular amongst the Ancient Greeks and apparently remains popular in some African areas, even amongst heterosexual couples, where fear of pregnancy is the stimulus. In it, the pleasure is all for the man. Either standing or lying down, the girl closes her thighs. After applying lubrication, the man pushes his penis between them, at the top of the thighs below the pubic bone, and rubs himself to orgasm. Take care not to hurt the girl’s testes. This ‘pseudo-entry’ can be performed from either the front or rear.