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!

34 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:

        Crissyi maybe offer those tgirls your throat and show them what a good girl you wanna be and how you’re looking to please them first and in doin so you’re getting enjoyment making them feel good. I bet one of them would get all horned up and won’t even ask just tell you to put that face down, ass up and welcome you to womanhood as she slides her dick in inch by sissy making inch till its up to the hilt. Grind on it a little and let her lay in you with her balls resting on your ass and then slowly work the whole shaft throwing that ass back and fucking that cock like a real slut should. Do all the work if you have to, it feels good and it’ll get you another invitation to service a cock and get your special sissy spots massaged by a throbbing rod (black if you know your place in the world) IF ALL ELSE FAILS, FIND A RANDOM GOOD LOOKING GUY ON THE STREET AND GET ON YOUR KNEES AND GRAB HIS COCK!! He may be surprised at first but he’ll fuck your throat once the initial shock wears off and he realizes you just wanna make him bust because you’re a good girl and you know your place. On your knees looking up at a cock with love and slutty lust. It’s all a mindset, try hypnosis, dating sites, if you wanna attract BBCs two toe rings and an anklet that has a spade or other spade jewelry like earrings, a necklace or bracelet lets them know you are actively searching for a fuck. Or a spade tattoo on an ankle, or sexy spot on your hip or breast. They make temp tats too so you can experiment with where you like it.

    • Jillian Tucker says:

      I’ve not had a cock in my sissy pussy but quite a few toys and a tongue and a couple fingers while a guy played with my little clitty. I chickened out but It’s happening soon!! Every good sissy needs a cock up her girly ass, if the way my toys feel is even a quarter what a throbbing black cock feels like draining his balls in me then I’m looking forward to the ride of a lifetime. kind of afraid I’ll like it too much and become a brainless cock drunk snowbunny that can’t get enough of daddy or daddy’s friends, co-workers, random dreamy guys that just want to take me in public in the store bathroom maybe a dressing room while my slutty ass tries on something sexy to really make daddy want to use me like his little whore. It’s also thrilling to wonder what it would be like to be property and dominated by my man/men and begging them to use their good little girl however they please.

      So my point is let your man fuck that ass girlfriend. You’ll love every second I bet and you’ll get closer to your guy and he’ll appreciate sliding in and making himself at home in you. Your body belongs to him anyhow, so let him play and make him feel good while he makes you feel like his girly little cock ornament.

    • 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. Rainbow Blade says:

    Not just for play, anal instruments have been used for medicinal administration for as long as it has been known to be effective. It’s very effective since the immediate area is very venous and any medicines applied are absorbed into the bloodstream very quickly, bypassing all filter organs, which makes it dangerous potentially.

    Actually, because of the very same reason medicinal applications are effective, using anal instruments for play/erotica is potentially incredibly dangerous. If you start bleeding, stop all instrumental use and either go to your local clinician, or use a cloth to apply pressure. It’s a very good way to bleed out if you’re not careful.

    To aid with that, I suggest also using an anal rinse agent like a bidet beforehand. Moist is best. Though, don’t wanna be soaked because it’ll make lubricant less effective.

    Yes, I’ve used anal instruments. It’s definitely a euphoric experience. I suggest this to those I do makeup and hair for, with the same caveats because the perils of carelessness are high.

  12. 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 !

  13. 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 ..it like a maraka inside ..I started keeping mine in even while at work or shopping ..it has trained me how to wag my little butt when I walk ..it 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 public..it’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

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