Wednesday, August 08, 2007

Q: My boyfriend won't let me finger his ass. I think he thinks it's "gay." WTF? A: Just do it.

This month, Details magazine has a provocative article about "demanding" anal sex. Read it here.

Dear Go-To Girl,

I really want to try fingering my boyfriend's ass when I'm going down on him, but he won't let me. He obviously doesn't know how good it feels or he would let me; how can I convince him? I think he thinks only gay guys like having their asses touched, but I know that's not true.


Want to Let My Fingers Do the Walking

Dear Fingerwalker,

Tons of straight guys get skeezed out by the idea of having you stick a finger in their ass, but I don't know if it's as much a fear of getting in touch with their inner gayness as much as it's a fear of something they think might be painful. Or painfully gay.

Chances are, at some point in his life, a guy has put his own finger in his ass, even if it was when he was a kid. If it felt good then, he'd still be doing it. So it's your job to connect the dots for him.

I don't know how many guys refuse to allow their girlfriend to put something in their ass; unfortunately, we don't collect statistics on that sort of thing. But most guys I know, if pressed, will admit to having tried it. It might be something that changes with age; the more experienced you get with regular, vanilla sex the more curious you become about trying new things. So if your boyfriend is, like, 22, you might trade up to an older model if you want to get kinky.

If I were you, I'd have a bottle of lube handy, maybe under the pillow or in your pocket, when you're going down on him. Get him to spread his legs and, um, surprise him with a well-lubed finger. Hopefully he'll like it so much that he'll let you stay in.

The capacity to experience pleasure with anal play is the same for guys as girls; you have to create an association in the brain that it can be pleasurable to have your ass played with. That's what makes the blowjob crucial.

If he really won't let you, I'd say let it go. Surely there are people who just can't have a good time with something in their ass. It's up to you to decide whether or not you want to be with someone who won't let you in. Having someone put their finger in your ass doesn't make you gay more than going to "gay reparative therapy" makes you straight.


GoTo Girl


WD said...

It's true: chances are if he likes to have a finger in his ass, he's discovered it by now on his own. But perhaps you can convince him to at least give it a try.

Make sure your nails are short and filed smooth so you won't hurt him. If you have nails and want to keep them, put cotton under the nail of the finger you mean to insert and put on a latex glove. A glove is not as sexy as your bare hand, but it's up to you.

He might be concerned about cleanliness. He could give himself an enema if that's the case. Fingering goes better if the receiver has an empty rectum and has washed well. Actually, several enemas will not only clean him out, but relax his anal muscles and make him ready.

Use KY Jelly, not a runny sex lubricant. A gelatinous lube is better for anal play. And use LOTS of it. Work it inside.

I suggest getting him excited first with some oral. Then insert just a fingertip and go slow. You can suck his penis at the same time as you finger him. A "come here" motion of your finger, moving the fingertip against the forward wall of his sphincter (toward the belly) about two inches inside, will stimulate his prostate. That's a selling point, by the way. Having his prostate stimulated will increase the intensity and duration of his orgasm. You can suck him off with your finger going in and out, or he can masturbate while you give it to his backdoor passage.

As for the "I think it's gay" issue, you should talk about that. He may be caught up in the unfortunate myth that associates anal play with homosexuality. In reality, anything a man and a woman do together is straight. You're really into his body so he should feel flattered.

Now, some guys just don't find anal fingering pleasurable, and that's ok. But I hope your boyfriend ends up liking it because you seem to really to enjoy doing it. I'm a straight guy, and for me, it is an absolute need. I wouldn't have married my wife if it didn't turn out that she loves to finger me (and lick my anus also). The fact that she didn't at first (she believed all the stereotypes, and had no experience with it) suggests that lovers can learn.

Anonymous said...

It is truly an amazing feeling. Very different from plain vanilla sex. Fortunately for me, my wife is into experimentation and she started fingering me two days back.. she could insert a whole finger yesterday and I'm really looking forward to some wonderful nights.

2 questions to the initiated:

I. What should we do after she pulls out for hygiene?

II. I can't seem to keep an erection while entering her vagina. While I could hold the erection for very long outside. We tried 3 times yesterday and laughed about it... but it could get frustating (specially for her)... any suggestions.

Anonymous said...

uh why cant u stay hard??

Anonymous said...

It's false: Chances are he has never fingered his ass and he will not discover it on his own. Masturbating is natural and that is something all guys figure out on their own. Not puting a finger in their bum.

Majority of guys do not finger there bum. Accurate statistics are hard but from my estimation being a guy i would say 70% would not finger their own ass. I have had my ass played with and licked many times now but I have still never played with my own ass. the reason is I have no desire with pleasuring myself that way but having a girl do it is a different story.

I was first awoken to the delightfulness of ass play when i was on a one night stand and a girl began licking and rimming my ass. To this day 23 years of my life had gone by with not even the slightest thought of ass play on myself, i had rimmed and had anal sex with girls though.

I think the best way to let a guy know that it actually feels good is not with a finger, a finger does have that something is entering feeling. A tounge does not enter and is alot easier to do. while giving a bj just slowly go lower licking, sucking the balls, and then maybe accidently lick a bit lower, lower, lower. go back up to sucking, kind of see how he is reacting.

I can guarantee he will like the feeling. Once he likes that a little rubbing and then bang bang next thing you know a finger. while this might happen in one session it will be better to do it slowly over a few sessions.

Great tip is anal play or a good place to start is when your bf is drunk. He is looser and more relaxed and he might not remember so if he likes it or not you will know after you atleast try.

I understand licking might be a bit more gross but it really does open a guys imagination to something new and different. If i had never had my ass licked that night i probably to this day would have not ever had anything up my ass or near it.

Anonymous said...

My wife loves to insert a finger up my rectum so much so that it's a daily occurrence even when we're both working in the bakery.
We have a 'quickie' when the boss isn't looking, and the whole finger up the arse thing actually speeds things along quite nicely.
It's quite an in-joke with us that one minute she's got a finger up my bottom and the next she's got her hands in the scone mix!
Yes we both know that, ideally, she should wash her hands before going back to work, but sometimes there just isn't time!
Anyway, none our customers seem to complain and most think our scones are quite delicious.
The wife's called Anne but I'm not really supposed to mention that. We live in Truro.

Anonymous said...

wtf truro? surely you're trolling. that is vile. i'm all for rule-breaking (i actively encourage it) but have some fucking integrity.

Cocerned said...

My husband of 18 years started taking my finger and wanting me to stick it up his ass and was wondering if he was cheating on me.

Cocerned said...

My husband of 18 years started taking my finger and wanting me to stick it up his ass and was wondering if he was cheating on me.

Anonymous said...

that is so fucking disgusting. i say fuck at work all you want, unless of course you work with food that you serve to others. that is a major health code violation. i would sue you so fucking bad if i knew you were putting butthole fingers in my pastry dough. you should both get fired for that, honestly. wash your fucking hands, dickwads.

Anonymous said...

Just wear gloves and everything will be okay. I prefer to tie my boyfriend down and then put latex gloves on. I have medium sized hands as a 19 year old girl, so I make sure I get tight gloves for maximum pleasure. I insert my finger until he screams in pain, then release and repeat 5-10 times.

Anonymous said...


Pleasure said...

I love giving anal pleasure. My boyfriend just started letting me lick his bum while he's fingering my bum. I had an orgasm for the first time last night and started crying because how good it felt. Anal pleasure is the best feeling ever. I can't wait until he lets me do more.

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