Having sex with a transgendered woman is almost the same as any other pairing: male-female, male-male or female-female in that it’s two humans coming together to share intimacy, strengthen the pair-bond, or just blow off a little steam. Emotions and desires are unique to the individual and must be respected above all for it to be mutually satisfying. That said, there are some general concepts that might be foreign to the uninitiated and the many variations of trans-types can be confusing to some outsiders. Communication is the most important piece of the equation, so talk to your transgendered partner beforehand and be honest with each other about your wants and dislikes. Even during sex to ensure that they are enjoying themselves be sure to keep communication wide open.
We’re going to speak in generalities here, so what might be true for most may not be true for your partner, but when in doubt, it’s hard to go wrong treating her like a lady, and as a reminder, safe sex practices are always a must no matter who you’re having sex with or how you plan to amp up the passion.
Transsexuals are unlikely to want to top their man. We feel that we are feminine and whether we have a penis or not, whether it’s working or not, we want to be treated like a woman and that includes being on the receiving end of any penetrative sex. If you’re a man who’s fantasy is having a shemale top you, which is a very common fantasy by the way, you would do well to hire an escort or let a cross-dresser or drag queen take care of this need – unless you can discuss it in advance with an agreeable Tgirl date.
Many TS women avoid getting involved with bisexual men, concerned that they’re only interested in having a “chick with a dick” for sex. Also keep in mind that if they’ve been on hormone therapy for any length of time it may have become smaller and unresponsive physically as well. If your partner has a penis and wants you to pay it attention, now is the time for you to do a mental inventory if you’ve always been a ‘straight’ man. Ideally, you would have thought about this beforehand, but there’s a difference between thinking about it in the abstract vs. having it staring you in the face. If you find that having that penis in the bed with you is ruining it for you, it’s important that you tread carefully lest you hurt her feelings. If you are able to get past the whole penis thing and she’s deriving pleasure from your ministrations, congratulations, you’ve successfully negotiated a major potential hurdle to maintaining an ongoing relationship with your transgendered sexual partner.
If your transgendered paramour is post-op, you need to be aware that her vagina is not self-lubricating so initially a little saliva will help prevent chafing as you rub her clitoris, which just like on genetic females, is an extremely erogenous zone. Any insertion must be done with a quality lubricant so as to make up for the fact that she cannot generate vaginal juices on her own. If her surgery has been recent, there is a good possibility that she will not be ready to have vaginal sex, but assuming you’ve gotten that far, oral or anal sex is a possibility.
Many transgendered women have experience with anal sex as it was the means that allowed them to most feel like a woman before they were ready or able to embark on the transition to female, the usual anal sex rules apply, just like with anyone else, prep work to ensure a hygienic experience, lots of lubricant and slow initial penetration.
Hopefully you will successfully negotiate the unique challenges of having sex with a transgendered woman, leading to an exciting and emotionally satisfying relationship for you both. That has always been the primary goal of I Love TS all along!
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