Josie Waverly

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reblog if you also sit when going to the bathroom

I am about to say something unpleasant but important: The first time you have a finger in your ass, it feels like you have a finger in your ass. What did you think it would feel like?

Actually, the first five, 10, possibly 20 times, it feels like you have a finger in your ass. But at a certain point, if everything goes right, it’ll feel like you have a finger in your ass accompanied by a spontaneous enhanced OMFG-AMAZING-Orgasm, better known as a SISSYGASM. It’s hard to know, because everybody’s different, and that includes each butthole-fingerer’s individual skill. So many sissy’s have bad first-time experiences and are fearful of it, but want to do it again. Some guy shoved it in without preparing for the action.

If you’re dating a sexually aggressive ass-centric person, rather than a nipple or leg or foot or right earlobe person, they’ll probably want to give you as many sissygasms as possible by fucking your boi-pussy like crazy.  You should never, ever do something you vehemently don’t want to do just because your partner wants to, and if you’re not ready for full-on anal sex, tell him.  Go slow.

But (BUTT! Ugh, sorry), if you want to experiment in that general area, here are some things to know about Base Camp 1, which consists of the stepping stones to anal sex: Fingers (anal fingering) and tongue (rimming, salad tossing, analingus).

1. It shouldn’t hurt. This is where lube comes in. It should basically just feel like you might need to poop. You don’t! (I hope you don’t.) Relax your muscles, and breathe. Use a lot of water-based lubricant.

2. Start small. The whole point of anal play is to keep it simple before working your way up. To prepare a bottom for sex play, start with fingers, tongue, or a very small sex toy designed for butt play.  An option is to purchase a Butt Plug Kit that uses several plugs, of graduating sizes, just for this training.

3. The person doing it should err on the shallow side. Everything that goes in should be “just the tip.” The nerve endings you’re trying to stimulate are in the anus — hence the moniker “rimming” — and not all the way up there, which is generally the painful part and also the part that makes you feel like you need to take a huge dump. Imagine it like a basketball hoop, and the ball should just be rolling around the rim of the basket, not actually making the basket. Does that help? I know nothing about basketball.

4. There shouldn’t be any rapid-fire movement immediately. Vigorous jamming of fingers anywhere should not happen immediately. So much of sex is fast — especially in porn — but anal play has to be prepped.

5. You can vary up positions. No, not all butt stuff needs to be done doggy style. It’s true it might be a little harder to get some solid eye-contact going on when face-to-anus things are happening. But! There are a variety of positions to try, like lying on your back with your hips elevated, or sitting on his face in reverse cowgirl. Move around until you find one that makes you feel most at ease.

6. Communication is key. The only way to know what works and what doesn’t is to be totally honest with you partner about what they’re doing. 

7. It’s not dirty. The anus and the lower part of the rectum actually have very little fecal material in them, which means it tends to not be nearly as dirty as you think.

8. That being said, you can totally clean things up. The key to anal play is comfort, so do whatever you need to help with any lingering anxiety. Using an anal douche is not harmful if only done once in awhile and might help you relax your concerns about your bowels.  You can use something as simple as warm water for a quick cleanse too.

9. It feels best when there’s some additional stimulation going on. He can stroke your sissy-clit, rubbing against your smooth tummy, and kissing your lips or your nipples — whichever feels best for you. While some sissy’s only need butt play à la carte, most femboys can’t come from anal stimulation alone until significant experience comes into play — making sure your prostate is stimulated by your lovers cock. That being said …

10. If you try it a few times and hate it, don’t keep trying it because you think it’ll eventually be tolerable. Assuming you have a considerate lover who’s invested in you feeling good, I think you’d know within the first five times whether you like it or not.  I’ve actually encountered sissy’s who hated receiving oral anal-stimulation initially but love it now, and it was because they were self-conscious. It depends on your levels of inhibition, your feelings about your partner, your feelings about your body. If all these things are good to go, and you just don’t like the sensation, you’ll know pretty fast.

So, start slowly with your lover.  Make sure he has lots of lube and you can relax.  Communicate with him as he enters you.  Try to keep him under control (which can be difficult for a submissive and petite feminine sissy with a bull twice her size or more entering with extreme excitement).

There will be a point, as you do this more, where his thrusts will feel wonderful, and his aim plus your positioning will allow you to experience the ultimate sissy affirmation – a multiple anal-orgasm that washes over you, makes your entire body shudder, and delivers you into an orgasmic high unlike any one you ever had with your stupid little sissy-clitty.