Process for ensuring nearly pain-free intercourse

So first off, I can’t honestly take credit for this as it was taught to me by an ex-girlfriend who was a MTF transgender. When I started down the path of dating and having encounters with CDs, sissies, and trans women, I was always the top and the aggressor. I had the occasion of being in summerlong relationship with a trans girl who was maybe a unicorn and encouraged me to get outside my comfort zone and try something different. In short, she wanted me to experience being penetrated (by her). It took me a while to warm up to this as I had tried it once before and didn’t really like it. That was a rushed encounter that I wrote about and regretted in my post” My first encounter as a straight with a Trans.” Anyways, all I can say is that chemistry and trust are both important to ensuring things go well with as little pain as possible. Oh of course there is going to be a bit of pain but with proper technique, other than the initial ‘stick’ and sting, pain is minimal.

The first thing to get clear is anal goes a lot better with a partner who is willing to rim and by this, I don’t mean just painting your inner butt cheeks with the tongue. Lick around it, make her feel wanted and comfortable. Lightly probe the rose bud very lightly. Open your mouth and enclose your lips lightly around her opening and create a gentle suction motion. Do this a few times and when the timing is right, lightly push in ever so slightly and gauge her tightness. This might take a few cycles but eventually, the muscle relaxes and you can slide in. Again, the goal is not totally tongue fucking her right away but eventually getting her to relax and feel comfortable having more and more of it inside. When the time is right, she becomes totally relaxed and this is your opportunity to slide all the way inside her. Of for sure, you will be hearing lots of different and sexy sounds coming from her which is a huge turn-on for the one providing the stimulus.

Once this is done, the next step is just to simply have him rub the cock against your ass cheeks and getting accustomed to the feel of it. A couple of pokes (but absolutely no entry) with the head against your hole does something to your sense of protection and further relaxes your mind.

The next step is of course generous lubing of both his cock and your pussy hole. Have him oil up his finger really good and slide it in a few times. Re-lube the finger and repeat a few times if necessary.

The next step is simply placing the head of his cock against your opening and either have him push in about 1 inch and stop or you can push back against him and stop when it begins to open you up. Again, STOP and remain motionless and let your sphincter muscles relax and get accustomed to being opened slightly. Stay in this position for 5-10 seconds without moving. Have him pull out, re-lube, and repat this one or two more times.

The next step is sort of a repeat of the last step but this time, have him push in slightly further, maybe halfway and again stop for 5-10 seconds. Repeat as necessary. The next step is (you guessed it) a repeat of the last step but this time, have him slide it in all the way and again STOP and remain motionless for the 5-10 seconds. I doubt there would be any need to repeat this last step since you should be very relaxed by this point.

After this final 5-10 seconds, your sphincter has completely relaxed and been opened up the same amount as his circumference and you should be good.

This was the exact process used by that ex on me and it went really well with minimal pain. She was not huge but around 7 inches and above average thickness.

Again, I cant over-emphasize the important role someone’s tongue has on relaxing you. Plus it’s a great gauge to use that shows when you are totally relaxed and ready…..good luck, try this an tell me how it worked. I’d bet any amount of money it will become your go-to process and you wont need to toy before sex or worry about pain ever again. Plus, hint-hint girls, no man wants to go down on a trans pussy that is all gaped out before we even have sex. I'd hazard a guess that most men want it tight so he can get it open and loose on his own, I know I do.