What's the best thing that's ever gone up your butt?

how has your life changed now you can no longer fag it up here like you used to?

a penis desu

>>25983673
What do you mean? Abcde

Oranges. If you put vaseline on an orange, let it sit on the orange overnight, the orange stops having a rough texture. Then you start with the gatorade bottle to stretch yourself out, then you push the big orange in and it feels amazing. Just the right amount of firmness.

>>25983776
Jesus christ, your asshole must be like a blackhole, I can't stretch mine no matter what i do. I can get three fingers in at most and then i'm done. It doesn't even feel that great to me

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How do I get into anal masturbation? I'm a fucking sissy that that enjoys wearing girl's clothes, I guess getting dicks up my butt must be the next step but I want to know what it feels like before trying it with someone and not enjoy it.

How do you say "penis" without getting b& for duplicate?

>>25983803
I started being an anal slut when I was like 14. I started with random brushes, then small deodorant bottles, progressively larger and larger things. Managed to fit my fist in my ass the first time when I was 16. Then I got more adventurous. Eggplants, lemons, apples, oranges, etc. Widest thing I put in my ass was this vitamin bottle that has a 3 inch diameter and it does not give at all, it's like metal. Used to have many videos of me gaping my ass and prolapsing but I deleted them out of shame.

>>25983891
Well, i guess i'll give you points for being dedicated to it. I only do anal stuff occasionally, or whenever my gf feels like it, so i'm still tight as fuck back there.

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>bought dildos, vibrators and prostate massagers for over a year
>although fapping with these in feels nice never managed to come even close to anal orgasm
just kill me senpai

>>25983819
Gry something that vibrates. You can have an orgasm faster this way than just rubbing. This will allow you to prove to yourself that prostate orgasms can happen to you. Then move on to rubbing it, then get some dick.

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Nothing goes in my out door.

My friend's dad's dick.

>want to buy dildo
>don't want to order one online since I still live with parents
>too scared to buy one from local sex shop

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I tried to give myself a prostate orgasm with my thumb tonight. Best I could get was a hot pissing feeling before I got bored and jerked one out like normal. I'm not that fond of playing with my own ass, I want a /cuteboy/ to play with. According to the map there's one about an hour away, but i'm a chubby NEET, so I won't bother.

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I wish I hadn't injured my anus years ago. It still hurts 10 years later after the first failed ass fucking attempt.

>>25985222
>go amazon
>buy large item for family, an example would be a screw driver kit
>add dildo do the order
>all arrives in one big box, any questions tell them its a gift
>unpack in your room, needless to say

>>25985721
Good idea, Sensei

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>>25985761
The next issue is storage and smell.

I cannot help you with these but just know, once you buy one, you will buy more.

>>25985673
Yeah anal tears take forever to heal
Ten years tho? Damn

>>25983891
>prolapse

seriusly was it worth to have damaged anus forever for few minutes of jerking?

how do you live now?

>>25983642
>Best friend once told me I must be the straightest guy on the planet
>Be exposed to traps in like 2007 or so when LineTrap/Bailey Jay and Alexis/Sarina Valentina were posted on /b/
>whyboner.jpg
>Porn collection becomes almost exclusively traps after a few years
>Have been insecure of my masculinity since age 11
>Keep seeing "I wish to be the little girl" phrase
>Ponder how much easier life must be as a grill
>Wish I was a grill
>Start fingering my bp
>No pleasure from penetration, only rubbing around it
>Fingered myself like a dozen times and can never get off from it
>Friend gives me her vibrating dildo
>Shove it up my butt
>No pleasure, just feel like I have to shit a vibrating brick
>Bought butt plug for Christmas
>Insert into pooper
>Discomfort for four hours, pain when removing that had me thinking I was bleeding for a moment
>Tried for the second time a couple nights ago
>Felt kind of nice but after three hours, a little discomforting
>Gut kept rumbling
>Pull it out
>Shit falls out on plug and all over my hand
>Tfw defective boipussy

>tfw when gf puts big dildo in your ass and fucks you until you cum everywhere

my butthole is special senpai
i'm saving it for 'the one'

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>>25983642
This. Crackstuffers gooseneck butt plug. It's quite wide(6cm diameter), but it makes me go wild every time I use it.