Fucking sissy’s tightest hole

Think a sissy only has two holes to use? Not if you’re my sissy. My sissies have three holes that I can penetrate and own. In this blog, I’m going to talk about fucking a sissy’s smallest, tightest hole. Whether you’re a solo sissy or an owned sissy, if you’ve yet to try this act of submission, this article is for you.

The ultimate emasculation

In case you haven’t worked it out yet, I’m talking about penetrating my sissy’s clitty. This is one of my biggest kinks. The perversion of it. The Dominance of it. Watching my sissy submit with a closed-eye whimper of emasculation and subversive pleasure as my hard, steel plug slides into her wet clitty – my fingers controlling every wicked millimetre that enters her. There is no force needed. In fact, it’s as if her clitty opens up to suck in that silver steel up to the hilt. And when I put my fingers on the underside of her clitty, I can feel each little ripple moving in and out. This gives me huge D/s thrills. I’m not just seeing my sissy penetrated, I’m feeling it too. One of those secrets of D/s that no one tells you about. *lustful smile*

So pleasurable, you might lose control

Done right, this penetration feels good. The sensation can feel intense at first and it can take you time to adjust. It may take you a few sessions, so persevere. But once your body starts to acclimatise to the sensation, you might be surprised just how arousing it is…all those sensitive nerve endings being stimulated in a whole new way. If you fantasise about having your masculinity destroyed, turning your clitty into a third fuck hole is a sissy goal.

Weapons of choice (and how to play safely)

The great thing about clitty penetration is that you can try it by yourself or with your Dominant. So, for all you solo sissies looking to take self-training to the next level, this is a good way to do it. Here are the things you’ll need to start.

<<All images should be clickable to take you straight to that product.>>

Toy steriliser – You can sterilise a steel plug by leaving it in boiling water for 5 minutes (and remember to let it cool before inserting it!) But I also like to use a proper cleaner that’s kind to your body as well as effective at killing bacteria. Also, wash your hands thoroughly before you clean the plug.

Small plug – I’d advise starting with a smaller plug. It gives you the best chance of a pleasurable experience from your first time. There are two basic designs – plugs with no hole and plugs with a hole through the middle that you can cum or pee through. The plugs with no hole can be slimmer for a beginner, but don’t just judge from the photos when you’re shopping. Read the diameter/circumference. Also, choose a plug with a loop or strong bend at the top so you can’t lose it inside you. This also makes it easier to hold and manoeuvre.

Here are three options to get you going.

1 Elegant, slim no-hole style

2 Through-hole style with dainty proportions

3 Solid plug, listed as suitable for beginners

Urethral lube – This is thicker than other lubes. Don’t assume you’ll be wet enough without it. Lube is vital. Your urethra is delicate. Treat it with respect. I’ve used this brand “Very Deep” with my sissy, amanda, and found it really good.

Getting started

I’m going to assume you’re doing this to yourself, but the advice stands for anyone. Before every use, run your fingers all over the plug to check for rough bits. Don’t insert anything less than perfect. Pee before you start as this cleans out bacteria, (unless having a full bladder is your kink…in which case, enjoy.) 

Assuming you’re fully sissified, take off your panties and get in a position where you’re relaxed, e.g. propped up on the bed. Have all the items handy, plus something to wipe your hands on as the lube can end up everywhere. Get hard, assuming you’re able to, as this makes it more intense. But if not, it’s possible to penetrate a soft clitty too. Being physically aroused also gets you wet and open, and this helps. Tip some lube into your pee hole. Lube up the plug until it’s dripping and very slowly ease the tip of the plug inside. And breathe. Then take your time, slowly letting it slide into your clitty.

Handling the plug

With a heavy steel plug, gravity should be enough ‘pressure’ to take it inside you if the angle is right. A tip for Dommes – take the weight of the plug as it penetrates your sissy. Don’t just let it drop in the first time as this might be a painful experience. If you feel a bit of discomfort as it goes in, add more lube and give it time. Don’t grip your clitty too tight as this can stop a smooth entry. 

This isn’t a ‘vigorous thrusting’ type of fuck

Especially not for the first few times. (Personally, for me, never as the risk of damage, pain and infection is far too high.) You’re aiming for pleasure. And it might take you a few sessions to emotionally and physically connect to feel this. Slow in and out is a sensual way to use the plug, especially the textured type. Go really slow and you can feel every little ripple. So hot. With the plug up to the hilt, you can also steady it with one hand and stroke with the other. There’s mixed advice about twisting a plug while it’s inside your clitty. Personally, I don’t twist a plug when I’m fucking my sissy. But you can buy spiral plugs, so you might want to do your own research on this.

Eyes open or blindfold on

Humiliation is such a fetish for me, I usually command my sissy to watch as I penetrate her with a plug…to see the inescapable truth that she’s no sort of man, she’s just a hole for me to fuck, that she’s a wanton little whore for actually enjoying it. *wicked grin* But closing your eyes and just surrendering to the feelings can be feminising in a different way, as you’re on the receiving end of penetration – a very sissy position.

Meet my ‘Gendr Fuckr’

This is my favourite plug. It’s no coincidence that this is the symbol for ‘Woman’.

This stunning piece used to be made by UberKinky but sadly they discontinued it. When I’m having a very D/ day, I’ll wear this out and about. I’ve had a few people ‘read’ me but that’s part of the thrill – flaunting my D/ status in plain sight to those who know.

Working your way up

This design has a glans ring, to help keep it in place. https://www.uberkinky.com/spade-drop-penis-plug-with-glans-ring-84600.html

Pink jewel plug
(Match it to your pink gem butt plug.) https://lustplugs.co.uk/collections/penis-plugs/products/stainless-steel-with-pink-crystal-penis-plugs

Pink vibrating plug
I can imagine this is a whole world of wicked fun when my sissy is banned from cumming. Either begging for more, or begging for mercy. *dark smile* https://lustplugs.co.uk/collections/penis-plugs/products/10-speed-vibrating-beaded-urethral-plug

Feeling inspired? Go and browse all the different plugs on offer and see if you can find the right one for you.


What are your thoughts on clitty plugs? Erotic? Scary? Leave a comment and let me know.


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