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I NEED HELP

this is my first time having anal sex. like I have some experience sucking dick but I've never taken it up my butt before. I've never even put anything up there. I'm getting fucked by my friend of 7 years after we started flirting earlier this year (he came out to me last year). I'm really glad it's him doing it because I trust him and it's his first time topping too. I'd been turning down opportunities from other people for years.

sorry for the blogpost but the point is I can 100% see a relationship forming between us and I really can't fuck this up and give him the ick or make him regret fucking man ass etc. I'm insecure about my ability and could use advice.

I'm most anxious about

>cleaning out
please explain how to do this like I'm stupid. everyone seems to have their own way of doing it so I could use a couple different opinions.
>lube
please explain what I need and how to apply it like I'm stupid. he is twice my size, pretty big length and girth so he's going to hurt me if this isn't done right. he's going raw if that matters
>my hole
I'm really insecure about how my hole looks :/ . it just doesn't look too good and there's a very noticeable skin tag from an old hemorrhoid. idk what I can do to make it look any better within two weeks.
>technique
how should I be relaxing moving my hips etc? he takes VERY long (like an hour) to finish and I'm pretty sure that would ruin my hole so should I ask him to edge first?
>cleaning up
I don't know what's needed for this and should we be fucking over a towel to catch the lube? I've never considered how much of a mess this could be

please help me /lgbt/ I can't ruin it with this guy.
>>
tops if you have an idea of how to make things hot for him (foreplay, what I can say to him during) please tell
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>>43090018
take a spoon of psyllium husk powder with orange juice every day for the next 2 weeks and then douching will be comically fast
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when
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>>43090043
I barely understand how to douche dude
>>43090054
he's flying in from out of state next thursday
>>
>I've never even put anything up there.
you haven't used a dildo or anything before?
it's probably going to be pretty painful and uncomfortable with this guy if it's your first time. hopefully he's ok taking it very slow
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>>43090096
this, at least try to play with your fingers, OP
>>
Anal sex takes practice, in fact you may not be ready for it since it sounds like he's coming over soon.

It's part of the reason I just don't like anal sex. It feels weird at first, not even really pleasureable, and it takes a long time to clean up and even longer to get accustomed to the feeling.

If you're dead set on doing it then you best get started today, like right now.

Douching is pretty simple. A douchhe is a device with a bulb and a nozzle. The bulb holds water or whatever, and the nozzle is inserted in your ass. Squeezing the bulb will shoot water up your asshole and it'll feel really fucking weird, and you'll feel like you have to shit. Keep squeezing the bulb and eventually the water will repeatedly squirt up your ass and dislodge all the fecal matter up there. When you remove the nozzle, your butt should already be over the toilet, and you'll shit a bunch of water combined with fecal matter. Do that a bunch of times. I believe they have internally safe soaps for this specific activity of anal douching but I've never used it so idk.

Once you've douched a bunch, just wipe your ass with a bunch of toilet paper and you're basically ready to shove something up there. Start easy for the love of God. Insert an anal plug for a while so you can get accustomed to the feeling of something up there but also very gently practice with something long like a dildo. Liberally apply lube to your ass and the toy before insertion and you're good to go. And I guess I also forgot to mention that you will need to use lube on the douche that you use to insert the nozzle. Anal sex feels really fucking weird and when you pull the dildo or whatever out of your butt it might feel like you're taking a shit. You kind of get used to it but yeah that's why I hate anal and feel that it's too much effort for not much reward.
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>>43090018
Eat more high-fiber foods, run 2 miles, and do Kegel exercises. This routine will keep your anal area clean, resulting in zero shit-covered penises for tops. 100% guaranteed.

You can apply a bit of ointment to your anus to increase sensation. Do this from time to time.

If you want your top to rim, buy the studio read coffee scrub, tastyhole flavored body scrub, or you can go DIY route with sugar, salt, or coffee grounds. Have fun!
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FUCKING QUEERS
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>>43090136
Is anyone gonna respond to this post I made? I made an effortpost because you were all frantically asking for advice and now I get radio silence? Cringe...
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>>43090220
Op really took your post to heart, immediately got started stretching out the hole
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>>43090240
>>
If the top’s penis is too large, you should breathe in and out deeply. Hold your nose closed with your hand; this can help your body relax and allow your hole to expand while you breathe deeply through your mouth.

>>43090220
I read it, but it sounds like you have more problems. Not typical bottoms.
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>>43090136
>>43090220
Sorry dude I genuinely appreciate it. I'm just waiting to answer multiple people at once so I don't need to spam the thread and repeat myself if more info is needed. But yeah I guess you and some others suggest that I should get some practice in first, which makes sense.

>>43090240
Nuh uh

I'm putting together a list of stuff to get, you said anal plug, dildo (I'll improvise for now) obviously lube. Silicone, water, oil?

>>43090140
Thanks bro I am /fit/ so I'll add kegels to my routine. Anything I should especially avoid eating?
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>>43090271
>If the top’s penis is too large, you should breathe in and out deeply. Hold your nose closed with your hand; this can help your body relax and allow your hole to expand while you breathe deeply through your mouth.

This should be standard for the gay sex education. It is quick and painless.
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>>43090274
Thanks for responding, and for the love of God use a liberal amount of lube. Go buy an anal douche from an adult toy store and do the stuff I said. Likely you won't be able to do anal or it might end up being too awkward or uncomfortable for the r first time so don't worry that's pretty normal.
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>>43090274
>Anything I should especially avoid eating?
Goyslops. Embrace carnivore diet plus some vegetables and fruits as well.
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>>43090322
I'm no quitter
I should add that I don't particularly care what I myself get out of it this is all about making his experience the best it can be. I love him that much
>>43090333
Awesome I'm autismo so I avoid anything greasy as a habit. Me looking good enough for him singlehandedly motivated me to start working out again btw
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>>43090353
Even still, you don't want it to be too uncomfortable so you should def use lots of lube. Your towel idea in your first post was a good idea I never really thought of that so yeah maybe also use a towel to quarantine lube and fluids
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>>43090353
>I avoid anything greasy as a habit.
yeah no seed oils for sure.

If you want to fry something, use Ghee butter
Make the food tasty as hell - use Beef tallow **Lard from the clean source is fine as well
Dressing anything lightly like salad - Olive oil.
>>
>>43090274
WATER BASED
if he takes as long as you say he does, I don't know if oral is the thing there or if he's genuinely just not very sensitive, ime silicone based can get really uncomfortable and "grainy" very very fast if you use it past its "tolerance". I wish i could say, idk if it's the heat, time in use, dissolving what little water is present in the lube, all i know is that it becomes an exfoliating abrasive immediately after failing as a lubricant. Oil based can be fine, i don't like them because clean up is super annoying. My personal go to is buying klube powder, or equivalent, and mixing my own so that it's quite thick and gummy, it takes a bit longer to dry. warming the lube container between your thighs is also a nice gesture, maybe just me but cold lube is an unpleasant sensation.
>>
>>43090018
>>cleaning out
>please explain how to do this like I'm stupid
Basically your ass is either good (solid, high soluble fiber, no spice, low/no meat) or bad (muddy/watery). If its bad just dont bother. If its good then use a lubed finger to open up and try to shit out everything in your ass. It will take a few tries and get shit on your finger, but you can just wash your hand. If it doesnt wash off easily it wont clean easily either so you might need to douche or give up
>>lube
Thick water based with no additives. I like the durex aloe vera one but KY jelly is fine too.
>how to apply
Lots on and in your hole. Lots on his dick. Lots.
>twice my size
Start super slow, stop for more lube whenever you need it. It can take 5-10 minutes to actually get it in properly. Breathe and relax.
>he's going raw
Absolutely do not. If you must, get on prep NOW. it needs a week to build immunity
>I'm really insecure about my hole
Sorry bro thats life, sex isnt always like the pornos
>>technique
Edge him first, edge you first. You're gonna last like 10 mins so sucks to be him. You'll barely be able to move, so demand small fast movements not long ones or you wont be able to walk the day after
>>cleaning up
Lube and cum get everywhere. Put down a towel, and shower after. You'll probably also need to shit out some lube too
>>
fill a water bottle with warm water and just blast it in your hole til shit dossnt come out. use vaseline and house hold objects until you can comfrotably fit four fingers in your ass. lala youre ready for sex
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>>43090379
noticing a distinct lack of tattoos
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>>43090396
>he's genuinely just not very sensitive
He says he usually never takes that long. He has to be shy. This time I told him to start nofap last week lol so hopefully he should be super sensitive by next week. I appreciate your lube advice going to go with water-based

>>43090398
>get on prep NOW
No no I trust him. I've been his first everything and I'm clean too according to most recent test.
>It can take 5-10 minutes to actually get it in properly.
Yeah it seems like he's going to have to take it very slow but it's not like this is a quick fuck or anything.

OK so I for sure need to work on stretching, kegels, need to go out and get some stuff. and next week I'll start a new diet. It's late for me now so I'm going to quit responding to posts until tomorrow am. Thank you guys
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>>43090508
Is he circumcised? Idk if there's something else about it like preference or whatever, but for me personally oral genuinely feels like a wet bag in the wind, partners have been frustrated my whole life with how hard it is to get me off orally, maybe he's got the same issue.
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>has never even put anything up their ass
fake bottom. youre not gonna enjoy it. i was masturbating by fingering my self as a kid long before i knew what being a tranny was
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>>43090582
He is circumcised. I'm saying he takes that long because last time we were together I unsuccessfully tried sucking his dick for a few days until the last day I spent a straight hour sucking his dick. We were almost late to the fucking airport lmao but finally I got him to finish. I'm cut too but I have a good amount of skin left so I've never needed lube to get off. He probably does. He insists that I gave good head
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>>43090604
I'm just scared of the poop dude I've for sure like massaged the area but fuck poop on my fingers dude. Mind you I'm cissoid
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>>43090018
>I've never even put anything up there
Get some psyllium husk and start taking it so that prep work for butt stuff is easy.
Get some lube and then slip a finger or two up there and see how it feels lol.
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>>43090018
Anal sex is fucking disgusting. How can you be such a masochist? Have some self-respect.
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>>43090018
just imagine that Elliot Rodger is topping you...
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>>43090619
i hate poop too, and the risk of making a mess is the only reason im not an absolute anal demon, cause it feels really good. anyway if youve never had anything there, start practicing now and practice every day until your date because at first it really just feels uncomfortable and not enjoyable. its a skill. your body will tell you to tense up but you have to learn to relax despite it. also make sure that your colon is empty not only because poop is disgusting but it also doesnt feel good at all if its not. lots of people tell you to douche, but douching is time consuming and unsexy, and thankfully not necessary if your diet has enough fiber and your colon is empty the natural way. so get psyllium husk and start practicing. you should be able to get three fingers in EASY. and when its time, take your time its not gonna go easy the first time when hes trying to go deep

>>43090659
yeah it is disgusting but it feels really really really good. besides butts and buttholes look good, its just the risk of poop that almost ruins it
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>>43090136
This is why I only have sex with women despite being attracted to men. What the actual fuck is this
>>
i love when a man plaps me in the butt. it brings me a moment of peace and disconnect from how much being alive sucks
>>
It's mostly mental. Don't be reserved or hesitant, you're kinda subconsciously making it more 'painful'. You gotta want that cock, and badly, too
>>
Hi I'm back

>>43090633
>>43090691
A lot of you say psyllium husk is super effective. Is it just a really good fiber? Adding that to the list
>>
You kids seriously need to get over your fear of human shit, how are you still this scared of something you have to encounter every day? Squirt a doucheful up there a couple of times but beyond that anal sex is supposed to be a little bit disgusting and weird, that's part of the fun of it
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>>43094226
Based take. I'm fine, I'm just much more concerned about him because he's still on bi catholic guilt programming

I tried playing with myself in the shower and I could barely insert my pinky up to the first knuckle (unlubed tbf). Am I fucked? sorry if that's tmi
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>>43093908
what's psyllium husk
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>>43094774
Fiber supplement. Its insoluble (you dont digest it) and a little bit sticky when wet. As it passes through your gut it helps thicken and bind everything together so that your shits are solid, smooth, and thorough.

Absolute cheat code for bottoming if you need to eat a lot of calories.
>>
One last bump and I'll let this thread die. I'm feeling pretty confident now. My enthusiasm will make up the difference
>>
>>43090018
this is probably the most comprehensive guide that I've ever read:
>https://github.com/regdude/anal
>>
>>43090018
also just buy xlube



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