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Butt Plug Sissy Guide

What is a Butt Plug?

Unlike dildos, which are designed to slide in and out, butt plugs are shaped to be inserted and left in place. The wide bulb slides past the internal anal muscle, while your body holds onto the neck.


5 Sissy Tips for Anal Play

Lube: Choose the right lubricant and use lots of it to ensure a smooth insertion.

Hygiene: Keep your butt clean by going to the toilet an hour before anal play.

Start Small: Start with small toys and gradually work yourself up into bigger ones.

Start Slow: Don’t copy porn. Listen to your butt and if it hurts, stop!

Build Up: Vibrating anal toys are perfect to spice things up and enhance anal play.


How to use a Butt Plug?

You might find warming up first helps – try stroking around the anus with a well-lubed finger, a little penetration with the same finger, or rimming if you’re playing with a partner.

Climaxing before anal play can really help relax you, too.

Cover your plug in water-based anal lubricant, then position yourself comfortably, either:

1. Bent over on all fours (aka doggy).
2. On your back with a cushion under your butt and legs spread.
3. Squatting over the butt plug on your feet or knees.

Holding both the base and shaft, position the tip at the opening of the anus, angled slightly towards your stomach, then gently push. You should feel the very tip enter you.

When you feel comfortable, push a little more of the plug in, moving your hand off the shaft and using just the base of the butt plug to provide any motion. If you’re still feeling comfortable, push further and let the slim neck of the plug sit inside you with the flared base resting externally.

What to do after the Butt Plug is inserted?

Once your butt plug is inserted, you can enjoy other forms of stimulation or intercourse whilst the plug rests inside you, or you might like to try grinding against it for extra sensations.

Alternatively, try moving the plug in and out of you, using the flared base.

You can leave your butt plug in for varying periods of time, ranging from 30 minutes to several hours, however we recommend that you take it out at least every hour to reapply lubricant. This way, you won’t experience any discomfort when moving around.

How to Remove a Butt Plug

‘Help! I can’t take out my anal plug.’ — Some people report that they tighten down, especially after they orgasm, which can make it tricky to take an anal plug out. Fortunately, there are some tips to help you take out your butt plug with ease.

Be gentle on the withdrawal, just like on the insertion. Hold the flared base in one hand and gently tug on it until you feel your body resisting. Keep that pressure and take a slow, deep breath. As you exhale, bear down in the same motion as when you go to the bathroom. If the butt plug slides out, great! If not, try it again, but as you bear down, gently angle it down 45 degrees, just like you did when you inserted it. As one side of the bulb comes out, angle it up 45 degrees.

When the bulb comes out, it’s easy to withdraw the rest of the toy quickly, but try to resist that temptation. Take it nice and slow so you can be gentle on your body. Even folks who are anal play regulars often report that going slow when they take their toys out works a lot better.

Clean your Butt Plug

Wash your butt plug with hot water and soap immediately after use and let it air-dry. Never share anal toys given the risk of transmitting infections, viruses, or bacteria.

You can disinfect your toy if it is made from non-porous materials like stainless steel or silicone and doesn’t have a motor. Simply boil some water and leave your toy in the water for about ten minutes.

Now with this handy information, feel free to plug (pun intended) into the wonderful world of sticking it up your butt! Plugs are a versatile resource to incorporate into your butt play, whether it be an adventurous warm-up to anal sex or a sensuous tool for expanding your rectum. The multitude of possibilities are endless, experimental, and downright dirty, good fun. So happy playing!

32 thoughts on “Butt Plug Sissy Guide

  1. mark says:

    Hello miss Ashley i am Mark 50 year old sisssy or wannabe sissy, i’v just been reading about butt plugs and how to use them as i’v never had one up my bum before, any tips?

    Mark x x x

  2. Colleen says:

    If you have not tried wearing a butt plug you do not know what you are missing. It will take any remaining masculinity from your body and feels sooo good!

  3. BrieBryant says:

    I perfer to place my fleshlight or synthetic pussy between my tighs and lube it so my man can fuck like a pussy , while looking at my trashy slutty wig and tuged/streched out lingerie, etc from being used and touch on for hours. Lol. Let him cum inside that silicone vag it wont matter to him and i cum constantly with my panties on, im always touch ing myself with no digression
    Also perfer high end breast form for titty fucking. Making my untouched virgin boi pussy a distant thought. Cause i always make’em cum ÷!!! Reguardless

    • crissyi wanna be says:

      HI im a closet sissy. now I know I can only experience happiness in life by becoming a sissys sissy, the problem is I c cant find one tgirl willing to fuck my virgin ass for free, and I cant afford to pay a tgirl to break me in. im craving tgirl dick so bad and don’t know what to do. I promise as as a tgirl turns my asshole into a pussy by fuckimg me into gurlhood, I will never wear mens clothing again.

    • Jillian Tucker says:

      Paula, girl you know it! My clitty starts leaking and my ass opens right up and gobbles my plug or dildos without coaxing like it used to. I had to play with it and tease her but now she likes being filled and stroked. I especially love grinding on my plug while rubbing my clitty and playing with my little nipples. Cumming with your ass filled is like nothing I’ve ever felt, I try not to even think of when I believed I was a boy. Cumming hands free with a cock sliding in and out of you stroking your sissy g-spot into a frenzy while you lay there remembering the day you decided you weren’t gonna lie to yourself anymore and let out your cutesy little slut to play and be played with. <3 😉

  4. Damon says:

    My first time never done it before I’m sad about dressing for a long while and just starting I have all kinds of questions one is kind of butt plug gets stock in you or what I mean is human spine all the way in and disappeared

  5. Sissyizzy says:

    I always try to have a plug in me or vibrator if I can’t then I have a tampon in but never go without something dont like feeling empty

  6. Nikki Matthews says:

    Love having my sissy pussy filled all of the time. Now up to a six inch circumference for that perpetual full feeling.

    • Jillian Tucker says:

      Lexi Taylor, ass big or small a good girl knows it will fit and makes it happen. Every queen is a size queen some just don’t know it yet. ; )

  7. Megan ryder says:

    Ive just started with plugs but dont get me wrong im already huge just from trying to fist myself. So my plug is big but even thoe i can get it in it doesnt seem to fully clear my sphincter onelce i begin to relax on it it aches and feels like its falling out even thoe its way in there are my sphincter mucles longer then normal or is this how its supposed to feel cause ive tried every other day and ince i did it before bed amd wokeup in the middle of the night haveing to take it out because it aches bad i tried just playing with my clit a little but it doesnt help.

  8. Melody says:

    your issues may stem from the plug being to heavy, your boi pussy not being acostumed to the shape or depth, alternitively the neck may be to short. For a “t” or “anchor” shaped base you will want the stem to be about an inch or so in order to clear both sphincters comfortably.
    good luck gurl

  9. LilyTgirl says:

    I have been using plugs in my Boi Pussy for years, I worked from small ones to now plugs up to 9.5″ circumference and love them. I usually stay plugged 24/7 with 7.5″ circumference plug, unless my man is using my Boi Pussy, it feels so good, I also have several leather harnesses to keep my plugs in place so never have to worry when out and about, the fullness feeling is awesome and it keeps your Boi Pussy always ready for use ant then everything feels wonderful ! Kisses

    • Jillian Tucker says:

      Lilly, I’ve found my thongs hold my plug in pretty well. That and it helps my slutty hungry little ass loves having something filling it up. I could be nude or commando and my plug ain’t going nowhere unless I’ve been fucked and gaped out that day. At that point though it’s undies on to help hold it there or asking daddy for more cock. <3 ;P

  10. Jillian Tucker says:

    Mistress, I would eagerly let you tie me up and have your way with my body. Slutty little throat for your pleasure and my face for your throne. I can put your pussy in heaven and I’ll let you fuck my face until you’re weak in the knees and thoroughly pleased. Then when you’ve gotten your fill I’ll beg for you to fuck me into sissy bliss with one of my toys or I’m sure that Mistress has a nice strap-on that she’s very practiced at ramming her slaves with. Spank me, pull my hair and call me your dirty little princess while you make me ask for more. I’m a good girl always but we can pretend I’ve been naughty so you can put this little slut into her place and punish me like I need. Or is it a reward? <3 It's most definitely a reward by the way. <3 *giggles*

  11. Lexi says:

    Hello, I’m Lexi, a 24 years old sissy and i want to thank you for the shop and for your advises, I can’t wait to try your plugs !

  12. Colleengirl says:

    I love plugs! There is something that changes in you when you start wearing them regularly. Start small and you’ll be craving to go bigger and bigger! The feeling of being filled is such a sissy turn on you’ll never stop using them!

    • Katrina Sparks says:

      Me too Melissa! The real thing is hard to compare too..giggles..but I did find this one plug that has these weighted balls inside it and when you shake your fanny you can feel them knocking around like a maraka inside ..I started keeping mine in even while at work or shopping has trained me how to wag my little butt when I walk feels So good that sometimes I’ll wait till nobody is looking or in the room and twerk like a little bitch until I wet my thongs in’s liberating ..but getting on top the real thing has gotten better because my man likes my new twerk giggles ..he gets there in half the time..I love making him happy mmmhmm

  13. Nikki_boagreis says:

    I gotta admit i was kinda skeptical or apprehensive about using one at first because it was a new concept, but i got to the point where i can’t get aroused without my butt plug. I’ll usually wear one underneath my thong panties, I’ve been wearing a butt plug on occasion for awhile and it almost feels natural doing so. I’ve purchased additional plugs in a wide variety of colors, can’t believe how amazing wearing one is or that i was nervous about wearing a plus. I like my dildo but i love my plugs, between my vibrator and plug im usually wearing something it just feels right. If you haven’t experienced wearing a butt plug it feels absolutely amazing, i love them so much.

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