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What to do on your first SEX

Amanda Valentine Dela Cruz

We were all once novices and today, I’m going to share with you some tips on how to deal with your first sex with your transgender date or if you’re a transsexual woman, your first sex with a man.  I’m going to divide it into 2 parts, being top and being bottom.  Please know that sex doesn’t have to include penetration but this is just for those who are seeking to try this level.  There are other wonderful things you can do in the bedroom that doesn’t include a penis inside a hole.  Please also know that the tips I’m going to give are for pre-op trans women or trans women who aren’t planning to under gender reassignment surgery.

So… how are you going to maintain the ember in the heat of the moment?

Let’s start with you being a…


Being a top is literally less invasive. You’re actually the one who’s going to explore uncharted waters… or waters that have been “over-charted” lol.  It really depends if your transgender date or the man you’re seeing has been around the block.  Anyway…  It’s imperative for you to know how to go in-and-out in a “Driving Miss Daisy” pace.  You also have to be versatile and know how to go “Fast and the Furious”.  What do you need? A good hip and butt exercise.  It’s important to have rhythm when you decide to be a top.  Apart from rhythm, you also need endurance.  Trust me, it’s less painful to be a top but way harder to be a top.  It’s like a workout but more.  What’s rhythm and endurance without a… HARD PENIS?


I mean no offense to people having erectile dysfunctions. It is so important to have and maintain a hard tool when you’re a top (for obvious reasons).  If you’re having problems staying hard, there are food supplements that may be able to help you with that dilemma.  Lastly, I know how the things I’ve mentioned above are so important to having a passionate bout,  but it will really help if you’re able to control your ejaculation.  Not only will a less than 30-seconds sex be disappointing, but it also makes things way less sexy.  Try to hold it for more than 5 minutes or if you’re going to finish so quickly, pause and change positions so you guys don’t have to call it a day too soon.

Now here’s something that needs more endurance (especially if you discover that your g-spot isn’t getting hit when being penetrated)….


Bottoming takes more courage than one could ever imagine. Especially if your partner’s penis has a girth that’s as thick as a Gatorade bottle.  Apart from courage, you also have to have very good hygiene in order to run things smoothly.  There’s no worse mood-killer than smelling something unpleasant while in the heat of the moment.  First off, you have to learn how to properly do an enema.  In my country, we have this thing called bidet spray which is common in household bathrooms.  This can be utilized to easily clean the pathway for your partner’s choo-choo train.  Fill your insides with water until you can’t hold it anymore and release everything in the toilet bowl.  Rinse and repeat until you see clear fluid.  Now that you’re all clean (not in a puritan way), you have to learn how to loosen up your hole.  Buy a medicated lubricant from the drugstore and loosen up your pathway by finger (depending on the girth of your partner).  Once you can put the ample thickness required and you can do an in-and-out without discomfort anymore, you’re good to go.  I know how an idle time can ruin a steamy blissful moment but not everyone is a masochist and will just take whatever they’re given in any given moment.  Lastly, if all else fails, there’s always foreplay and that stuff never gets boring.

Good Luck!



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About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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