A Big Stretch – Anal

Note from the author

  • This article is based on a conversation with another StoryVa.com (Lit) user during which the author was going through stages of inserting a large butt-plug and documenting what she was doing in parallel. The author thanks the other Lit user for his support in turning this private conversation into a Lit article.
  • Although the author was documenting what she had just done, present tense is used throughout for stylistic reasons.
  • The original conversation has been collated and lightly edited for clarity and to improve the flow. Typographic errors have hopefully been fixed. Some further introductory material has been included. Also images that were featured in the original thread have been changed to links.


So, I’m gonna be inserting myb-Vibe Snug Plug. It’s a size 5, which is the largest size for a vibrating Snug Plug, though they also do a non-vibrating size 6, which is even bigger. The size 5 is probably more than big enough for most people. It is not a beginner’s butt-plug.

The main part of the toy is a thick cylinder, which is nearly two inches across. This has a conical section at the top to aid insertion and then an inverted conical section below, which tapers to a long stalk and the handle. The two cones and cylinder together span about four and a half inches. If you include the stalk and handle, it is six and a half inches long.

The main problem with this plug is not the length, it’s the width, nearly two inches of sphincter stretching fun. Even though I have inserted this particular plug many times before, you have to respect a two inch wide butt plug. Also, I have neither used this toy, nor had anal sex in a few weeks. My sphincter is notorious for tightening up, so this may take a while.

What I’m gonna do is write things down as I go through the process. While I write this paragraph, I haven’t started yet. I’ll need to pause at numerous points. When I do, I’ll write some more about what is going on.

By the way, this is gonna be an accurate description of what it is like to insert a large anal toy, not a pornified version where it slips in easily. I hope that’s OK. I’m actually really doing this, not making up a Literotica story.

So here I go. I’ve stripped and am on my bed. I have put two layers of towels down and have a roll of kitchen towel to hand as the lube can get everywhere. I’m gonna begin on my back, but suspect I will need to either crouch over it or go on all fours at some point. The butt plug is lying next to me. It’s matt black and looks large and a bit intimidating. It isn’t very tapered like some. Once it is in you, that’s great and you feel so much more full. But it makes insertion tricky. I never turn the motor on for insertion, it doesn’t help and I discover it distracting.

So no plug for now, just fingers and lube. I’ll write again to tell you what I did before I move on to the plug itself.

Stage One

I lie back, spread my legs, raise my knees so that my feet are flat on the bed and tilt my pelvis upwards. The bottle of lube (water-based) is on my stomach. It’s my travel bottle and about half full, that should hopefully be enough. I flip the lid and pour a little onto the tips of my first two fingers. Then I reach down and run this in circles around my asshole. I get some more lube and do the same, this time easily slipping the tip of one finger inside me, followed by the other. I wriggle them a bit, enjoying the feeling. Then I withdraw, lube them more and this time push them deeper into my ass. When my knuckles touch my asshole, I waggle my fingers. Oh that tingles.

Now I lube my first three fingers and insert them, still not much resistance. I twist and turn my hand trying to loosen my muscles (it’s better if someone else does this for you, they have more freedom of movement). There is not much point in trying four fingers on one hand, it won’t loosen me enough. So now on to something new.

I lube the first two fingers of both hands and slip them in with the nails of one side facing the nails of the other. It’s tight doing this and I close my eyes and breathe deeply. Then I pull one hand away from the other. At first I can only separate them a little. I pause, let myself relax, and repeat. After a few goes, I can maybe move my fingers a quarter of an inch aside. I rest again, breathing heavily. Then I move both hands through ninety degrees and pull up and down. I rest and repeat; rest and repeat.

OK, that’s about as much as I can do with my fingers. Time to move on to the actual butt plug.

Stage Two

I pick up the butt-plug. It is heavy, one of the things I like about this make, you are all the time aware of its weight, even if the buzzer is off. I cannot withstand taking it in my mouth. It is big and I have to stretch my lips to accommodate it. It tastes slightly of my ass, but that just turns me on. I suck on its thickness and rub my clit. Rubbing my clit seems to help to relax my anal muscles.

OK enough fetish stuff. I pull it out, hold it vertically and drizzle lube onto its conical top, adding it to my saliva. I stroke the lube downwards and twist my closed hand around the plug spreading it. I do this a second time. My hand is covered in lube and I rub this on to my asshole. I am not optimistic about the first go. I have only got it in first time once and ended up bleeding a bit. I don’t like my ass bleeding, so I’m gonna go slowly.

I put the toy between my legs, angle it correctly and push it against my hole. Nothing much happens. The angle of the tip is shallow and it’s not easy to get started. I push again and feel myself yield a little. I stop the pressure and lube the tip and my ass some more. The next time I push, I can feel my sphincter is a bit softer. I bear down hard. As I try to push against the toy with my ass muscles, this counterintuitively makes them soften more, stretch more. I push harder with my hand and bear down again. I feel my ring start to open. But it’s hard work.

Time for a rest, more lube.

Stage Three

So progress to report.

I rest a little, close my eyes and will my body to relax. Then more lube on the toy and me and we try again. The bearing down is helping, but I can feel sweat oozing from my pores with the exertion. This is not easy.

But I am rewarded I can feel my ring open. Just a little, but open. I withdraw the toy and explore with my fingers. I am gaping very slightly. Using a hand mirror, my ass is about a quarter to a half an inch open and twitching. I rub lube inside myself, which tingles and try again. This is good. I vary the angle of the toy, constantly stretching a new area. I bite my lip and bear down even more. I can feel it slipping in to me. I am opening more, accepting the large intrusion. It is going into me at a slight angle, but it is going in. My sphincter is stretching beautifully. Maybe I’ll make it on the first real go.

But no. A sudden sharp pain has me pull the toy out immediately and wince. I feel teardrops roll down my face. Fuck that hurt. I feel around again and dab myself with kitchen towel, half expecting it to be stained scarlett. But no real damage thankfully. I realize I have been holding my breath and exhale loudly, taking a deep breath straight afterwards.

I’m a bit shaky, but we are almost there. No time to wimp out. I take some time out to rub my clit, it feels soothing. I breathe deeply and think how nice it will be to masturbate with the toy buzzing deep inside me.

Stage Four

So big anal toys are not for the faint hearted. No pain, no gain. I compose myself and am ready to try again. This time I stand on the bed and then crouch down on my haunches, this spreads my ass-cheeks wide. I steady myself with one hand on the bed in front of me and push the butt-plug up into my ass. I checked before and my gape was now nearer an inch, not far to go.

I close my eyes and try to channel the force. What would Rey do?

It’s somehow easier to bear down like this as well. I can feel the toy almost immediately slip further into me. I push up and bear down and wriggle the toy trying to work it in. And at some point it feels like my ass surrenders. Suddenly the resistance is less and it almost feels like I am sucking the toy into my ass. The tip is in, the widest bit is in and all I should do is to push it further, no more stretching. I can just enjoy the feeling of this thick rod probing me more deeply. I’ve reached the end on the cylindrical section and my asshole closes slightly pulling the bulk of the toy inside me.

The long stalk is still sticking out, but it is not too traumatic to push this flush with my butt.

Success. And I tell myself what a good girl I have been.


  • The article references specific products. This is purely for illustrative purposes. The author is not endorsing these products and has no affiliation whatsoever with the companies involved.
  • Readers should acknowledge that use of anal toys involves risk and that injuries can occur. For this reason, caution is advised. The author in very experienced in the use of anal toys and such experience takes time to develop. The author accepts no liability for any problems arising from the use or misuse of anal toys.
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