Initially, question posted to Bro. Tarte.
So, to all bros, bring it on.....need your gists.

I am a fan of butt fuck.....female and ladyboy.

I am not as experience as you since you are doing this full time and mine only at leisure when opportunity strike.
Past anal encounters were with GFs and ladyboys who had their arse fuck not for the first time. So penetration into 3rd hole with less hassle.

Need your expertise on this.

Recently I had 2 civi gals who allow me to anal devirginise them.

1st was a failure. Proper lube but she was unable to take the strokes. So had to pull out after less than 1 1/2 strokes and she rushed into the toilet to flush it out.....thanking me later for cleaning her 48 hrs expired bowel...
She tried to relax her anus muscle but when my cock went half way in, not to mention the screaming and hard slapping from her !! Easier said than done.........

Gal 2, supposedly plan anal devirginise this weekend.
So, my question is how do you go about getting a successful butt sex from an anal virgin?
By successful, I mean at least I can get > 10 strokes of pumping.

A fren told me to insert my finger first to relax her anus (mild fingering) before inserting my schlong.....but this from a fren who nvr done anal...  so fuck him!!!
Easier said than done.....

Total nood to anal devirginise....so please pour in....

You should watch Maria's AV on her first anal experience to see how its done

Ah, now unlike mongering experience, here's something I'm pretty well versed in.

Bad news first: Most experiences are not going to go as smoothly as you like, regardless of how you prepare. That's on the girl and not you... Unless she's a truly dirty girl who has experimented with all sorts of things up there before then she is not likely to be prepared for the fully engaged, at least half way stroking sensation.

However, there's a fair few tips that you can take note of which will make the experience perhaps not perfect, but at least not a disaster.

1: A few drinks beforehand never go astray to relax her and take some of the edge off.

2: Foreplay is still important. The anus has a pretty impressive ability to stretch out when the girl is aroused and some digital stimulation is occuring. Get her nice and wet with DATY and start out with some regular penetration until she is nice and horny. The endorphins and engagement of the lower area in general will take away a lot of the pain and shock.

3: Start to finger her anus as you fuck her normally. If there is an under-sized vibrator or dildo handy then even better. Will get the elasticity going.

4: It is ideal to start out in missionary anal, not the ever popular doggy anal. This position allows her to relax more and allows you both a greater degree of balance and control over the depth of penetration. You do NOT want one of you to slip and shove it in too early, there will be blood.

5: Do NOT start by popping the head in like you would with a more experienced ass. Ease half in, then back out, then 3/4, and back out, a few more times then finally when she's settled *plop*. From here, it's easy.

Anyway best of luck to you, hope it works out better...let us know.

I am not sure about all the other things although I've tried a lot and I have no idea if it had a good or bad effect.  From my experience the #1 thing that will help you succeed in this mission is "willingness" from the girl, simple as that.  Devirginizing an asshole for me has been sucessful for me 100% of the time when the girl is 100% willing and wanting to give you that something special.  Most other times failed with the exception of 2 sluts who wanted to just try something new.

My best one:  A married 32 year old MILF who has never experienced an orgasm from a man her whole life.  I gave her, her first orgasm via 45 mins of nonstop DATY.  I tapped that literal ass that very same night because I did something for her, she wanted to do something for me.  It was the tightest asshole and I went slow and deep.  Creampied her asshole and she was complaining about being constipated.  We did it a few more times after that but she never truly enjoyed it, although the last time she said it gave her chills (not sure what to make of it, good or bad? you decide).  I always enjoyed it, and I went BB every time.  I don't regret it, she was my mistress for a good 1.5 years.

hunter bro
i have a few caus girl friends who loves anal
Anal sex is not for anybody but if she's willing to try then why not.
first is lots of foreplay with relaxes the mind and make sure there is lots of touching the anus area.
lube is important................while fore playing slowly insert one finger in her ass.
Alternating this between fingering her pussy and ass.
i would also suggest in a vibrator which is little smaller then you cock so once she is use to the finger then you can go upsize.
once the body and the mind are both relaxed then its time to try.
and make sure you don't pump it like 100km/h...............take it slow and slowing increase the pace.
Anyway...................good luck...................may the anal force be with you

Slow and easy wins the day, even then it's not a skill every WG can master, I'm assuming since she's asked you to do the honours, that she is willing and up to a point mentally prepared.

Buy a small and medium butt plug, glass if you can find it otherwise a soft silicone and some sort of clitoris stimulator. Try and get her to get used to having the small plug in for an hour or so prior to your booking, perhaps you could agree to be the first customer of the day. 1st session or two just have a standard session and see if you can get her to O with the plug in, then work your way up to the med. plug before working your way up to the LB. When your fucking her up the ass try and start out with the position she's most comfortable with, (usually missionary or doggie) and get her to massage her clitoris with the stimulator while this is happening.

Make sure you use a good quality lube, (tarte will no doubt be best to advise you here as to brands available locally). Wash the plugs afterwards in hot soapy water and air dry. With a silicone plug use a condom during use.

Any kind of virgin requires lots of patience.

Hope this helps and good luck.

[ Last edited by  atomic3d at 2-6-2010 14:10 ]

I once had anal long, long ago with a GF. I went BB. Big mistake. She mounted me from the top in CG and it was really tight and felt great. She was in pain but a real trooper. Pumped away for about 3 minutes but when she got off I saw these brown stains on my dick. Wasn't sure if it was shit but this really put me off anal sex for life. It also ruined a good relationship because I could never look at my GF the same way again after seeing what I thought was her shit on my dick.

[ Last edited by  geoduck at 2-6-2010 16:30 ]

Thx to all for your advice.


Very true. Anal is something sacred to the gals. Fear and fobia to discomfort, nastiness and potentially pain.

I find it harder to anal a WG than civi gal. Like sexpert said, gal is willing and wanting to give us something special when they have feeling for you and wanting to please you.


I shall need to get a vibrator this week and maybe some WxxD.....

When I was at college, one of my housemates was bi, and he always placed a saucer of poppers under his bed, saying the aroma helps to loosen up the sphincter muscles!

I'm glad I never asked you about your good ole days !  

you mean she was a real pooper

Anal sex is fun to try but once the novelty wears of i much prefer good old fashion pussy pumping

Atomic bro.............nice dummies you got there ( pic )

hunter bro

all the advise here is good. get her to drink, foreplay, lube up, mish anal.

i also had the experience of BB anal and had shit on my stick

one thing is always do that is not mentioned here is that when i'm taking her pussy doggy, i lube up my thumb and insert it in her ass. and i've done this to many girls, and it works.

once you can get your thumb all the way in her ass, just go in and out 10 or 20 times, then quickly lube up more and insert your dick slowly. 9 of 10 times, half the head gets in, so just let it stay there and let the hole stretch, then pump a bit and get it deeper 1 cm at a time.

hope this helps. good luck!

Have you people never heard of anal enemas or douches?

It is what porn stars use beforehand as well as not eating before so they don't get a chocolate pork sword. Except for max hardcore video I once saw where he pulled it out and it was covered in shit and even the pornstarlett was horrified when he wanted her to suck it.

I'm sure the question on everyone's lips right now is: ... And did she?!

Yep....alll good and most of the info are fresh to me:

1) mish is more anal friendly than doggy
2) intoxicate her with alcohol
3) thumb fuck her anus for a good while, instead of using the middle finger.
4) using plug and silicone dildo


I think I am all set......

DaBest, didn't shit on the dick really put you off? It ruined anal for me forever. But then if the dick is the size of your thumb as you had mentioned, think the girl would hardly notice you've made the switch .

gives a whole new meaning to having a "BANG"...

This video may help you Hunter...
LINK

This book is said to be very good...
LINK

[ Last edited by  TonyToro at 2-6-2010 18:03 ]

Think most of the bros here are referring to having anal with GFs and not WGs. As such, the anal was a spontaneous act in the heat of the ML session.  If you tell your GF before hand you're gonna fuc* her in the ass and she better go and clean out the shit, think she'll freak out. I think WGs would already have cleaned themselves as they know what would turn a punter off.

just my 2cents;
I had to devirginize few civi girls ass.

I would not recommend a butt plug.
You have to make her horny to avoid the brown surprise.
take her pussy doggy style, and while you're there, lube her anus, and get 1 then 2, then 3, thumbs there. That's like a final count down. Make sure you leave your thumb for few seconds there, then start vibrating it, that helps her relax. Try placing some slaps as well, that would increase her tolerance for pain.

Now the first penetration is the tricky part. If all previous steps are done successfully, and the girl is not phobic, then mish is the way to go, try to put her legs confortably upwards, or if she's flexible on her shoulders, and go in. first time is always slow, no bumping until she's really comfortable.
If the girl has a phobia, then , by experience, your best bet is to let her lead, usually in CG, she'll test her limit few times untill she realizes there's nothing to be scared of.

Now, as her first timer, it's a huge responsibility. Depending on you, this girl will or will not make other bros very happy, so don't fuck this up. I'm always pissed off when agirl tells me she tried it once and would never try it again. All I think of at that moment, another fucker got the magic key but chose to break in.