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First Time Anal for Cross Dressers

If you are new to anal sex, let me be honest with you, bottoming can hurt. But, the good news is it only hurts if you do not know what you are doing. The bad news is since you have never had penetrative sex before as the receiver, odds are you do not know what you are doing. It is a completely new bodily sensation, being penetrated, and it takes practice. Unfortunately, sex education typically does not cover same-sex sex or butt play, and it is seldom discussed in mainstream media. But I'm here to help you turn that pain into pleasure.


1. Lube is your best friend


There is no such thing as too much lube. Especially for your first few times, you want to be as lubricated as much as possible, to help your man slip right in.


2. Cut your fingernails


Are they cut now? Good. Now cut them shorter and file the jagged edges. You will want finger yourself to loosen up, and long nails could scratch you. Your nails cannot be too short.


3. Practice in the shower


Now that your nails are freshly manicured, practice fingering yourself in the shower. It will help you get used to the sensation and prepare you for the real deal.


4. Fight the urge to clench


Your natural response will be to clench. You need to fight this urge, but you don’t need to push out either; you just need to relax. Your body will naturally loosen up with repeated penetration.


5. Go slow


Take your time to get the whole thing inside you. Don’t start off by letting your partner ram you. Take as much time as you need to get comfortable, and when things start to feel good, then, and only then, you can ask him to go a little faster and harder.


6. Pee beforehand


The first time I bottomed, I was convinced I had to pee repeatedly. Also, side note, the harder you are penetrated, the more it feels like you have to pee. This is due to the prostate stimulation. So pee beforehand, and expect that feeling to occur. You’ll understand the sensation more with practice.


7. It can feel like you are pooping


The only other experience you have had with your anus thus far in life is pooping. So it is no surprise that, in the beginning, it often feels like you are pooping which is also why you feel a natural urge to clench. The association with pooping will go away with repeated experience.


8. Clean beforehand


This has more to do with psychological pleasure. You will not be fully present in the moment or enjoy it if you are worried you are unclean. You can use an enema if you would like, but it is often unnecessary. A soapy finger or baby wipes works too. You can also gently flush the area out with a slender ear syringe. It uses less water than an enema or douche and can clean you out fully.


9. Express exactly what you want


Communicate what feels good and what hurts. Tell him to go faster or slower or to switch positions. Especially for a first-timer, the bottom needs to be vocal and in control. Anal sex feels different for everyone and there is no way your top will know what feels good without you directly communicating your needs and desires.


10. Wear a condom


And of course, safe sex is pleasurable sex. Always wrap it up.

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