# Ramming a dildo up yr boyfreinds ass



## Gudj

It seems weird that this thread doesn't already exist, but hey.

Anyway, does anyone have any ideas on how to properly ram a dildo up my boyfriends ass?
(or similar activities).


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## bote

god, there are at least three threads about this already, use the search function.

but seriously, ask nicely? wait till he´s blacked out? probably you´ll need to trade favours...


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## nivoldoog

Lube... and a reach around


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## formaldehydekat

don't listen to the poster above me to be true punx you shove it in dry and thrust as hard as you can
it's even better if it isn't consensual


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## Pilgrim

Remember.

Its better to give than receive.


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## Gudj

I don't know.... $30? Seems steep.


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## Gypsybones

well if things are tight, then it may be worth putting in for it.


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## Pilgrim

Can't put a price on an orgasm though.

How kinky.


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## nivoldoog

$5, but you got to spit on it yourself. If you want her number let me know...


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## Franny

Gudj said:


> Anyway, does anyone have any ideas on how to properly ram a dildo up my boyfriends ass?



The only advice I have is to lock the door if you're at his mother's house, because otherwise his mother might walk in and stand there open mouthed before passing out in a puddle of her own urine.


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## DIAMONDRAILS

Well, this thread is down right SICKING!!! I mean really people is there nothing else to talk about??? It would be bad if someone under 18 would pop up and find this thread... Mods better think about this stuff!!!!!


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## wildboy860

get 'em drunk 1st!


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## wizehop

nivoldoog your too funny man! although the question doesn't sound too serious so hard to take seriously...are you trying to figure out how to get him to let you do it or how to put it in?......The ramming part is pretty straight forward...just ram it...as far as how to get him to do it...maybe pick an object he likes as apposed to a dildo, pickle, hot dog - you know dildo sounds so feminine. Or get one in a color he likes...fuck even a glow in the dark one!
Also maybe start small, like a pencil (eraser side) and work your way up to one of those double enders.


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## oldmanLee

Yep,gotta admit that this is going to be one of the livlier posts when it gets going good!


..........and franny,enquiring minds want to know.........was your post based on theory,or a somewhat badly timed adventure?


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## Gudj

wizehop said:


> are you trying to figure out how to get him to let you do it or how to put it in?.




I was surprised that alot of people interpreted the question as "how do I convince him to let me" instead of what I assumed it was: "how do I do it in the safest and most pleasurable way possible". 

I'm mostly waiting for MattPists answer.


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## oldmanLee

Just goes to show,Gudj;that as out there as some folks think they are,there are still lines that seem to be waiting to be crossed.


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## Rash L

start with a well manicured pinky... then move the ring finger and so forth. and always use a good lube....


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## JahDucky

Funny story, really. So one night i get the idea to put my dilly in my partners keepster. He's wasted and when hes wasted I can try really dirty, naughty thing on and with him(he wont remember and if he does he can pretend it never happend) And so im doing the damn thang and he says I have to stop cause Im hurting him now(i was usually pretty gentle when doing this to him but this time round i was way too wasted which resulted in animalistic buttfuggins)......two days later I had to go to the store to get him some roid creme and those hemme pads they give ladies after having babies...

true story!



Oh yeah and Rash is totally right. And then once you have the dilly in his keester stroke the shaft and tickle the balls....hell squeal like a little piggy! SSQUEEEEEEEEEEEEEEEEEEEEEEEEEEEEE!


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## Franny

oldmanLee said:


> ..........and franny,enquiring minds want to know.........was your post based on theory,or a somewhat badly timed adventure?



That was not theoretical advice. That was an adventure so badly timed that it did end up in piss soaked carpet and immediate eviction.



Gudj said:


> "how do I do it in the safest and most pleasurable way possible".



Aside from the locking the door if you live with easily shocked people advice, all I can offer is lube. Lube is wonderful stuff. Prevents the anal fissures and all. I don't have a prostate though, so the pleasurable part I can't help you with. And since you mentioned it, now I'm also curious what Matt might say as you seemingly implied it would be either useful or hilarious.


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## spearchukka

Some good advice here......pencil (eraser first), pinky finger, ring finger, tube of lube, dildo........so I taped them all together and it wasn't that bad. I personally like to wrap my CCG around a large orange, little bit of tape and Roberts ya Mothers brother..........vitamin C levels are right up there!


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## JahDucky

I can help with the pleasurable spots. 

The P spot(yes...prostate) is the male equivilant of the g spot and can be triggerd by applying preasure to the taint as the man ejaculates but the best way to get it up and going is to take a finger or two slip em in just a little and give it a tickle. You dont have to go to far in...maybe 2 or three inches is fine(like the g spot)


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## rideitlikeyoustoleit

Start small, make sure it's clean, and be gentle until they are relaxed.

Oh, and LUBE! Seriously!


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## Rash L

yay for taint massages!


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## oldmanLee

Franny,my hat's of to you girl!Remind me some day to tell the story of why one ostrich skin engineer boot was hung up in a rose trellis in North Little Rock .........


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## dirtyfacedan

This thread needs more trains.





No...wait...maybe not.


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## xmaggotx

so...im actually going to post a serious response, because i've been thinking of making a zine on this (and prostate health) anyway...

rubbing or pressing the taint during or before orgasm wont stimulate the prostate. however, pressing the taint before and during orgasm DOES stop a man from cumming (while still experiencing the orgasm, he wont ejaculate)... but thats another subject. i personally have a cheap prostate stimulator butt plug for this purpose, since its difficult to do a reach around in most positions, and any amount of fingernails can hurt if you aren't doing it to yourself. i have a water-based lube (personal choice since it doesn't contain animal glycerine). i bought a small toy when i got mine since it had bn a while since i had done any anal play, but now i kind of wish i had gotten a larger one. maybe somewhere in the middle...ask your man.

my toy has a small loop on the end for your finger to go through, which makes it easy for me to use when my girlfriend is on top or fotr her to use when i am on top... but its a matter of personal preference. as for the shape, its nice to have something with a bulbous end, and a curve...the male "p-spot" is in roughly the same place as its female counterpart. 

as for prostate massage not during sex...he should do it himself first, a good position in on the knees, head down. then use the middle finger (obviously lube it up) and basically go in a couple inches, while applying pressure towards the stomach, until he finds a walnut size lump (i had a hard time finding a lump myself, but i definitely felt when i hit the spot) and slowly apply a "come here" motion while applying pressure, starting behind the prostate, and extending down past it. just keep doing that and eventually he should feel like he's going to pee...he wont, but sooner or later a small amount of discharge should come out of his dick. its asically just the non-sperm part of semen, and its actually build up, and full of toxins that he just expelled from his body, so wipe that shit up and throw it out. thats a pretty general idea ut i think its pretty good...let me know if you want more info


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## smellsea

formaldehydekat said:


> don't listen to the poster above me to be true punx you shove it in dry and thrust as hard as you can
> it's even better if it isn't consensual


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## Rstank

DIAMONDRAILS said:


> Well, this thread is down right SICKING!!! I mean really people is there nothing else to talk about??? It would be bad if someone under 18 would pop up and find this thread... Mods better think about this stuff!!!!!




kids under 18 have sex all the time what about this is any different than the subject of any under age sex.....it didnt say shoveing a dildo up your under age boyfriends ass it said a very general topic.....and to point out many people think it is unethical but in my oppinion if you care about a male partner as much as he cares about your pleasure you would know that his ass has all the senstive areas and if you want a mind blowing orgasm thats where you look for a man.....post in general topic under age sex im sure youll have a nice discussion there but your comment is neither constructive or helpful it seems just blissfully ignorant of the male anatomy....maybe we should have the mods look out for unhelpful post rather than ones that arent appropriate for age groups....and i dont know any way under age kids that would make a profile for a traveling site anyway.....8yr olds hoppin trains and shit......ridiculous how could they climb up in that box car anyway


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## Rstank

xmaggotx said:


> so...im actually going to post a serious response, because i've been thinking of making a zine on this (and prostate health) anyway...
> 
> rubbing or pressing the taint during or before orgasm wont stimulate the prostate. however, pressing the taint before and during orgasm DOES stop a man from cumming (while still experiencing the orgasm, he wont ejaculate)... but thats another subject. i personally have a cheap prostate stimulator butt plug for this purpose, since its difficult to do a reach around in most positions, and any amount of fingernails can hurt if you aren't doing it to yourself. i have a water-based lube (personal choice since it doesn't contain animal glycerine). i bought a small toy when i got mine since it had bn a while since i had done any anal play, but now i kind of wish i had gotten a larger one. maybe somewhere in the middle...ask your man.
> 
> my toy has a small loop on the end for your finger to go through, which makes it easy for me to use when my girlfriend is on top or fotr her to use when i am on top... but its a matter of personal preference. as for the shape, its nice to have something with a bulbous end, and a curve...the male "p-spot" is in roughly the same place as its female counterpart.
> 
> as for prostate massage not during sex...he should do it himself first, a good position in on the knees, head down. then use the middle finger (obviously lube it up) and basically go in a couple inches, while applying pressure towards the stomach, until he finds a walnut size lump (i had a hard time finding a lump myself, but i definitely felt when i hit the spot) and slowly apply a "come here" motion while applying pressure, starting behind the prostate, and extending down past it. just keep doing that and eventually he should feel like he's going to pee...he wont, but sooner or later a small amount of discharge should come out of his dick. its asically just the non-sperm part of semen, and its actually build up, and full of toxins that he just expelled from his body, so wipe that shit up and throw it out. thats a pretty general idea ut i think its pretty good...let me know if you want more info



amazing post my friend very helpful :applaud:


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## JungleBoots

my best suggestion, is to give him the toy first, and let him figure out how to do it. practice makes perfect.

aside from that this is my breakdown of the anal play process.

COMMUNICATION! use words like "ready?" "you relaxed?" "how do you like that bitch?"

pay attention to body language, and the grunting noises, it might be hard to tell the difference between crippling pain, and glorious pleasure. (which tend to come hand in hand with anal)

painless anal is possible though! if you are patient, and careful. THIS IS NOT SOMETHING I RECOMEND DOING FOR THE FIRST TIME WHILE DRUNK, though he being drunk might actually help a bit.

but other than that, everyone says lube, water based works well for me, but really when it comes down to it spit seems to be the crush the competition, you dont run out and it actually seems to last longer than water based. which type of lube you prefer is something you and he need to figure out along the way.

like everyone said, start small, i go with the pointer finger wriggling them around a bit, you will feel when he relaxes, then after that i move on to two fingers. for me, two fingers is good enough to insert a dildo, a sizable one too... but for most anal newbies keep putting more fingers, four should do the trick for sure. but i mean once you get to four... you might as well toss in the thumb and straight on to fisting... (lol joke lol)

this is the point you check to make sure there isnt any poopie inside, that not only is disgusting, but also painful and unhealthy.

before you insert the dildo you have to make sure it is sufficiently lathered in your lube of coice, any dry spots will stick and cause hemeroids. once you get the dildo/cucumber in there move it in slowly, He will know when hes ready for you to pretty much start fucking him. so again COMMUNICATION!

once all is well start pumping slow, it should start to feel pretty good so long as he didnt get hurt along the way. (the pain of improper butt fucking lasts a while, and is intense, so it can really take a long time settle that pain down again.) once it starts to feel good, at least in my experience the ass is somewhat self lubricating (lol) but add lube at his discression, especially since you cant feel it yourself.

once shit is nice and happy go to fucking town on his ass. It will hurt if you go too deep, especially if you go too deep too fast but i wont lie anal is definately for masochists. and for me the harder the faster the better.

now massaging the prostate is nice, but if you do it too soon and too hard it actually hurts... alot. The prostate is NOT the equivilent of the G-spot, it feels nice but hes not going to have an intense orgasm from it. Like alot of people said the prostate is best to be massaged when near orgasm. for me the pleasure of anal has little to do with the prostate, its more to do with the inward and outward motion of the object and the depth of penetration.

so i guess now that ive dropped some serious TMI on you ill return to my pornography as all of this anal play talk has gotten me somewhat arroused.

kthxbai


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## partysummer07

Geez Gudj, I'm glad that this is the very first thread I read on the forum that you urged me to join.

To make this post relevant to the thread I'm gonna go ahead and agree with everyone who said start small, go slow, and use lube.

Also, maybe fewer people gave advice on how to do it "the safest and most pleasurable way" because of your use of the aggressive language, "ram."


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## Poe Boy

Don't listen to these friggin guys.

1.) Use a strapon.
2.) Use lube.
3.) Slap his ass until it's really red
4.) Ram the thing in
5.) Either grab a handful of hair, or put on foot on his head
6.) Do a lot of aggressive grunting, pretend you're loving it
7.) Keep yelling "Fuck me back, bitch!"
8.) Pull out and using your "sweet" voice tell him "Ok, your turn!"


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## Gudj

Since the description for the Sex & Relationships section got updated, something about this thread has been lost.


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## wizehop

spearchukka said:


> Some good advice here......pencil (eraser first), pinky finger, ring finger, tube of lube, dildo........so I taped them all together and it wasn't that bad. I personally like to wrap my CCG around a large orange, little bit of tape and Roberts ya Mothers brother..........vitamin C levels are right up there!


 
YES! :applaud: Let me know when your in the souther US man


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## wartomods

anal is bad for your rectum's health


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## Shakou

formaldehydekat said:


> don't listen to the poster above me to be true punx you shove it in dry and thrust as hard as you can
> it's even better if it isn't consensual



OMG You're awesome XDDDD


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## Matt Derrick

hmmm, i thought i had already commented on this thread, but apparently not.

originally, i couldn't think of a good description for the sex and relationships section, so made up the description quoted above as a joke. it was only a joke, but im actually really happy to see the positive and helpful comments about this subject. this is exactly why i created this section so we could talk about unusual subjects like this not generally covered in our community (cept maybe in zines).

personally, ive never tried it, but im not opposed to it 

p.s. the forum section's description was changed a while back to something a little less in-your-face.


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## MiztressWinter

Wait...you've never tried a dildo rammed up your ass? Or anal sex. lol that could be read a few diff ways lol


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## femmeriotgrrrl

I don't know a whole lot about this personally. I do know that anal dildo or strap on sex with men is called pegging. A great site for advice is Sexual Health, Sex Toy Info, How-to Guides, Sex Tips and Advice - Good Vibrations. I think consent is really important like taking it slow asking questions and lube(water based if yr using condoms or gloves, silicone if not).


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## Eviscerate

DIAMONDRAILS said:


> Well, this thread is down right SICKING!!! I mean really people is there nothing else to talk about??? It would be bad if someone under 18 would pop up and find this thread... Mods better think about this stuff!!!!!



oh we are sorry for offending your delicate sensibilities. some people like this so stop being so goddamn closeminded and just accept that some people dont think the same as you.


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## vegetarianathan

Why in God's name is this still alive after almost 6 months? Probably just the shocking title. After I read it I HAD to come and see what people suggested. With that out of the way:
I agree with Poe Boy, but I would change the last step from "Now it's your turn" to "Say ahhh!" like the dentist says XD


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## Matt Derrick

Eviscerate said:


> oh we are sorry for offending your delicate sensibilities. some people like this so stop being so goddamn closeminded and just accept that some people dont think the same as you.


 
hell yeah! also i think it's hilarious that diamondrails thinks we're going to get in trouble with minors for a thread like this. it's not pornography dummy!


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## Gudj

Matt Pist said:


> hell yeah! also i think it's hilarious that diamondrails thinks we're going to get in trouble with minors for a thread like this. it's not pornography dummy!


 
I'm pretty sure that her post was a test. It happened within a couple of days of IBRR leaving the site.


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## bananathrash

you need to drink a buttload of cherry koolaid, turn into the hulk, roar, and then caress his anus.


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## Crocodile

I've noticed a lot of people have said to begin by lubing your finger and then wriggling it around. Before you do that, it's a good idea to gently massage the perimeter of the anus with the finger until it relaxes, especially if he's never done anal before.


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## BanMatt

I have a boner.


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## shwillyhaaa

uhm..is this a joke? or are you serious? i cant tell cause you said it in a vulgur way... if your gonna ask something serious...try to make that clear


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## wildboy860

oh this post is dead serious. at least it was to start out.


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## dirtyfacedan

dirtyfacedan said:


> This thread needs more trains.
> 
> No...wait...maybe not.


 


Really? Nobody got that?

Anyways...

Anal sex can be fun..whatever you are. It can also be a scary, and not very fun place for many. Lots of fun can be had doing "bad" things. However..for some fucked folks..bum secks can be a place to hurt people. A place where it's not about sex...but about how much pain can be inflicted. People need to know partners, and protect themselves from unwanted encounters!


We all need to be safe with the people we are having sex with, and make sure we are not going to get hurt. Unless that's your thing, and even then, we also need to make sure we are not going to get hurt! 


We all need to be able to trust the people we are in risky situations with, be it riding trains, or riding cock...be safe, and be on the look out for your riding partners!! RIDE SAFE!


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## shwillyhaaa

trains and asses.. not good for the bowl functions im sure... 
safety is an overall line to make sure you draw in any situation... 
im sure id have a more divine message to leave here if i could see the rest of the thread but for reasons beyond my knowldge
i cant.
so fuck.


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## Diagaro

Toasting in epic bread.


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## MiztressWinter

All I can really tell you about are my personal anal experiences. I'm sure that it works differently for everyone. 

LOTS of lube. I can't stress that enough. I tried a couple different kinds, and I like plain old ky jelly the best. It's best if we start out in doggy style position, having him put just the head in at first, and then letting me slide back until it's all the way in at my own pace. For some reason, it always hurts when the head is put in, but once it gets all the way in...it's a GO from there. As hard/fast as my bf can give, I can take. It's just getting past that first initial penetration and getting it all the way in. 

Once we start out in that position, I like to switch it up. Sometimes lying on flat on my stomach is very good. I also enjoy being on my back, on the edge of the bed, with him holding my legs up as high as possible in the air so that I can play with my clit at the same time. I actually discovered that (with clitoral foreplay to stimulate my clit and get me swollen) that I can *squirt* like this. Ha! Took me 33 years and lots of experimentation with an awesome partner to figure this out. 

I think the key thing to anal is being relaxed. If you are tense, or your muscles tighten in ANY way it can be quite painful. I don't think being drunk would necessarily be a BAD idea if you are the type of person that gets very relaxed when you drink. Do whatever relaxes you, smoke a joint, have a drink, have your partner massage you and lots lots lots of foreplay to get you stimulated and excited. Also, in the very beginning, we started out with him using his fingers and building up. When I could tolerate 3 we went for the deal.


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## lostinspace

DIAMONDRAILS said:


> It would be bad if someone under 18 would pop up and find this thread... Mods better think about this stuff!!!!!


 
this is squattheplanet, right? who the hell is bitch complaining about "what if the kids see this. go to facebook if you concerned about being PC


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## JoshyWashy

I'm 12 and what is this?


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## shwillyhaaa

my god dude you brought the bathroom picture back haha... just joking but ive been waning to say something about your avatar for a while so yea. lube=yes jack in the box tacos=better la=eh not so much (funny story)


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## MiztressWinter

lostinspace said:


> this is squattheplanet, right? who the hell is bitch complaining about "what if the kids see this. go to facebook if you concerned about being PC


 
Even though i agree with this statement, let's not call someone out (by calling them a bitch). thanks


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## dharmabumpkin

im all for personal exploration, but shouldnt it be his decision? bring it up, but no means no and shit. report back and let us know how it goes!


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## 3t87

lmao> i tried this avenue with a girl i was dating and it was a no-go, she was very exploratory and open to new things but that was a no-go she insisted if i were to do that i would be in for a ''surprise''i did not want,so this was option was easily put to rest, be smart and stay safe!!


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## LeatherTrampGypsy

BanMatt said:


> I have a boner.







This is the best post, evAr!!! Good job.
'Preciate everyone coming together to help someone out. 
Good luck with the anal man.


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## CardBoardBox

I like how this thread has waaay over 2000 views yet only a handful of replies. everyone seems to think "OH, what IS the best way??!" hahaha. Some good advice though.


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## Teko

Gudj said:


> I was surprised that alot of people interpreted the question as "how do I convince him to let me" instead of what I assumed it was: "how do I do it in the safest and most pleasurable way possible".
> 
> I'm mostly waiting for MattPists answer.


 
Honestly, just buy a small to medium sized vibrator, and a water based lube. On the not so popular side of anal stimulation, you might want to get a anal douche, or things could potentially get messy. Use a generous amount of lube, be gentle and if he likes it, be creative. As long as you are : 1. Not damaging anything inside, and 2. Not causing him discomfort. Things will be fun and enjoyable. Hope this helps.


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## bastardmaker

formaldehydekat said:


> don't listen to the poster above me to be true punx you shove it in dry and thrust as hard as you can
> it's even better if it isn't consensual


 marry me?


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## Aypathy

i enjoy cucumbers myself


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## Heron

m0ar! #4933 -


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## Harvey Steelbanger

dirtyfacedan said:


> This thread needs more trains.
> 
> 
> 
> 
> 
> No...wait...maybe not.



Bahahaha.... Well done sir.


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## infekt

Crocodile said:


> I've noticed a lot of people have said to begin by lubing your finger and then wriggling it around. Before you do that, it's a good idea to gently massage the perimeter of the anus with the finger until it relaxes, especially if he's never done anal before.


 
TRUTH. 

Also. Lube. Use so much lube you think its overkill, then add more. And don't start with an 8" monster dildo. Think about how you'd feel with that in your ass.


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## thewitt

go slow and tell him to push his asshole out like he's about to take a shit. he'll love it


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## ayyyjayyy

DIAMONDRAILS said:


> Well, this thread is down right SICKING!!! I mean really people is there nothing else to talk about??? It would be bad if someone under 18 would pop up and find this thread... Mods better think about this stuff!!!!!



are you serious? LOL.


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## acrata4ever

if you flip his gay switch he may dump you


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## RO71

What loved about this heading was its listed right after the serious worldly political subject of Occupy. Guess I'm jaded. 
Well my ex, love of my life used to want to have me do this with a number of objects, always freaked me out though-the sh*t factor I guess. Just use the Do Unto Others logic: go slow, be careful, use lube and watch for that sphincter pressure. Curious: is he expecting this or not? Becuz if this is a surprise attack, I want no part of giving advice!


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## Eng JR Lupo RV323

Nice necro.


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## scales

don't listen to these people i bet they have never shoved a dildo up there asses before as a gay man let me tell you be careful it hurts a lot dont go and shoved it in there make sure it's well lubed up use you're fingers and lube to loosen the hole up and take you're time because if you don't you might rip his butt hole and give him hemorrhoids its very painful and its nasty to the touch


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## wizehop

How about kegel balls, I got a story for ya.

So a few years back we was partying, and while high on E and god knows what else I end up with one in my ass. Of course since I'm stoned I somehow end up forgetting about it. Next day (maybe the day after) all is good, and I'm starting to get cramps. Long story short I sit down to relieve myself and I hear this ping sound as this ball bounces into the bowl, and then I remembered....

True story, not gay but open to everything...no more kegel balls though, cant handle the responsibility.


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## scales

thats funny and yes those damn kegel balls are amazing


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## scales

aim picturing you taking a shit and bloop sound ahaha that must of been funny i can't believe you weren't able to feel it


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## DankyKidd

Easy does it! Yea def start with a finger or two. The more tense he is the more its gonna hurt him. Gotta get him to relax. Start with his fav foreplay. Get em riled up, then start with a rim or something. Then easy does it. Start with pinkie, always have ur nails cut, and lube it up. Ask him what he wants less,more,fast,slow.


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## Odin

::meh::

This is almost as cool as the licking bloody vagina thread... I think I'll go and hide out there for a bit.

https://squattheplanet.com/threads/licking-bloody-vagina.11484/page-8


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## Doc Road

Personally,good ol fo play; start with kissing ears,neck,bum,than toss the salad,play the rusty trombone,with a bottle of water for optimum saliva,and work your way up too... Sky's the limit isn't it. You'll be in there like swim where. As long as one is adventurous and hang ups are let go,new,glorious experiences are at hand. And for the receiver,one word;submit.


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## Corinne

thats hot...


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## todd

than toss the salad,play the rusty trombone,

I had to google that shit....LMAO


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## PriusFuck

LOL this thread was started a hundreds years ago and people are still replying, an important topic i guess.


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