Ask Isabella Q&A: Anal Penetration…Some Things You May or May Not Want to Know
Thrust EXTREMELY gently into her because any asshole will make the tightest vagina in the world feel like a loosey goosey.
I’ve received several questions specifically asking about anal sex. The 4 individuals I have chosen to quote have asked questions that I think
the general collegiate population can relate to. Some of the questions and answers overlap in content, but I figure that slight repetition can
only do more good than harm. So let’s begin!
Max writes:
Hey Isabella. Ever since the first time I experienced the angelic and joyous feeling of penetrating my penis through the lips of God’s most
beautiful gift to earth, I have had an unyielding curiosity of what anal sex feels like. Only to compound my curiosity, my past relationships
have been replete with inexperienced girls who refused to let me anywhere near their rear. I’ve tried all the conventional methods; I would
vocalize my emotions, use scented candles, and even one time I tried to slip a finger in during cunnilingus, another futile attempt. Therefore,
once again I must consult my oracle for her well polished methods. Can you help me gain access to the females’ most treasured back door?
Thanks again!
Isabella writes:
There are two things that are preventing you from having anal sex:
- The notion that it will hurt the girl
- The issue of trust.
Anal sex requires a fun, open-minded girl. Don’t try to fuck her in the ass on the first night (unless she brings it up of course). Bring her back
for 2 or 3 nights AT LEAST before even popping the question. This is going to take time. You want to gain her trust. Don’t even think about
telling your boys about anything! Not even after the first night. I know you boys like to talk. Control yourself and be discrete. It’s about the
sex, not the bragging right; and if sex really is a passion of yours you will abide by that code. People will respect you more for it in the long
run anyway. And if you do tell a few friends which I’m absolutely positive you will do, make sure they keep their mouths shut. Otherwise
your mouth will fuck you over and you will never have anal sex again. Guys’ lack of discretion is what makes it so hard for all of you to get
some. Girls are extremely concerned with reputation. Start respecting the girls by not talking about them and they’ll feel more inclined to
reward you. If all girls were guaranteed confidentiality, we’d all be DTF. And that’s a fact.
Pop the question while you’re drinking and smoking— be honest and tell her you’ve never had anal sex— it will ease the pressure for her.
You also MUST emphasize how discretion is important to you. And if it’s not important to you, change your ways immediately. Gossip can
really hurt people, Max. Not to mention it prevents girls from putting out. Promise her that you won’t tell anybody; after she’s been so great
to you, the least you can do is respect her privacy. Acknowledge all of her apprehensions like gossip, pain, and privacy. Put everything out on
the table. Show her that you understand where she’s coming from. Her name should never leave your mouth after the deed is done. NEVER.
If she says “no” or even “I don’t know” to having anal sex, then drop it forever. Don’t pester her. Reverse psychology can work in your favor
later on. Genuinely make it about her and not the anal sex. Good things happen to those who wait.
I’m not going to lie to you. Girls are deep. You’re going to need to work for it and put in the time. But when the girl does say yes, be
prepared. Have lube and ultra-thin condoms ready. You want to drench your dick in lube as well as her asshole. Thrust EXTREMELY gently
into her because any asshole will make the tightest vagina in the world feel like a loosey goosey. Wine and weed will relax her muscles as
well as her ass tremendously, so those are good things to offer her beforehand. Just make sure you don’t go overboard on all of the drugs and
alcohol yourself; you don’t want to have erectile dysfunction. Also, when you pull out, don’t do it too quickly, the asshole is like a suction if
you catch my drift. We’ve all read the Tucker Max nightmare. Odds are that nothing bad will happen, but it’s in your best interest to take
precaution.
Men really are from Mars and women from Venus. In order to get her to physically do what you want, you need to meet her halfway and tend
to her psychological needs. That’s how it works.
Selena writes:
Ok Saturday night I ran into a guy that I’ve gone on a date with and made out with on our second encounter. Anyway, after I left the bar on
Saturday he picked me up from my house and took me to his place. Things got really heavy and he decided to do that shocker move* on me.
It felt really odd but it ended up enhancing my climax. When I came it felt great but I thought I was going to go all over his bed. I don’t
know if it was because he was occupying my butt space or if I really had to go?
He asked me to do the same for him and I obliged…but the first/last time I did that for a guy was 5 years ago, and at that time I was
completely coked out of my mind (so it wasn’t an awkward experience). So my questions are: is that “having to go” urge normal? And have
you ever come across guys who have asked for anal stimulation?
*shocker move = “one on the clit, three in the slit and one in the shit”
Isabella writes:
YES YES YES YES YES. Good news, it’s just a side effect of the sensation; you’re not actually going to go during the sex. I think anal
penetration has its way of putting indirect pressure on one’s bladder. Just pee at some point before having anal sex and it should lessen the
feeling. Keep your bladder as less full as possible. But of all of the too-many-to-count instances in which I have had anal sex and not taken
pre-peeing precautions, I have never peed. So no worries. Peeing beforehand is just to prevent you from getting paranoid.
I have been asked to finger boys’ assholes as well as lick them. Believe it or not, anal penetration arouses many men. There is actually a way
that men can come from anal penetration and it really “milks” them for everything they’ve got. It’s not just a funny scene in Roadtrip, it’s
actually true! I have never met a man willing to go this far, but the prostate is located in the anus and if you put enough pressure on it, he can
in fact ejaculate.
There are also theories about a male “A-Spot” located in the anus enabling several minute-long orgasms without ejaculation. But I cannot
say there is scientific proof of this male a-spot. Actually, there are people who believe the female g-spot does not exist either— but I am
obviously not one of them. Anal pleasure is actually natural for a man; it just takes one really comfortable with his sexuality to welcome it.
Desi writes:
I’ve tried having anal sex a couple of times and have only been able to go at it for ABOUT 2 minutes before screaming at my guy to take it
out because the pain is just too, too intense. The first time he was pretty reckless about it- just diving right in and thrusting away…not cool.
So very, very not cool. The second time, after doing a little research on the matter, I told him to just put it in and chill out for a little while so
I could like..stretch out and kind of mold around it (so I’ve heard?), but even then I just couldn’t deal. And I’ve used PLEEEEENTY of lube
both times. Anyway, is this much pain to be expected? Am I giving up too soon (i.e. do I need to keep at it for another few minutes before I
can actually get remotely into it)? Do you have any tips on what could make it an overall less painful, more enjoyable experience, or is it
possible that anal just isn’t for me/ are not all sphincters created equal? By which I mean could I be biologically incapable of comfortably
taking a dick up my ass? Because that….would be unfortunate…
Isabella writes:
It’s definitely worth noting how big your guy’s dick is. I prefer resorting to anal sex if and when I’m dealing with a smaller penis. But there
have been many times when I’ve had anal sex with larger ones. And yes, there have been times when a huge dick hurts me so much that I
have to say, “It’s way too big, turn me back around.” Phrase it in a way in which you are complimenting him, and the mojo won’t die. The
truth of the matter is that an asshole is MUCH tighter than a vagina, as you know from experience, and sometimes “big” is just too big. An
asshole does not stretch the same way a vagina does. I think it was really careless of your guy to just started riding into your ass without
initially being gentle because going too hard can really tear something in there and permanently disable you. Anal sex has its risks (and I’m
not talking about STDs) and he REALLY needs to be aware of them. (I have graphically explained the risks at the end of the article).
Regarding increasing your asshole’s tolerance, leaving his dick in there motionlessly isn’t going to stretch you out, which explains your
dissatisfaction with that tactic. His dick needs to somewhat be in thrusting motion in order to create any space at all. Indulging in marijuana
and wine beforehand will definitely relax your muscles and loosen you up a bit more. If it hurts you too much— then that’s quite alright.
Your asshole and his dick may not be a good match. His dick may be too big for you; it’s happened to me a number of times. Or, you may
just not like anal sex; it is an acquired taste. If anal sex were universally liked, then everybody would be doing it… and clearly not everybody
is. So there’s absolutely nothing wrong with the fact that it’s not tickling your fancy. Every woman’s body works differently. But I do think
everybody should at least try it.
Amy writes:
Anal sex – I have recently discovered the pleasures of a finger in the butthole, but I’m scared to go full throttle and have anal sex. Do you
enjoy it? What are the benefits/differences between it and vaginal sex? I’m also afraid of the stigma of being a girl who has anal sex.
Isabella writes:
I enjoy anal sex because I feel his dick indirectly hit my g-spot from the back angle which is half stimulating and half makes me feel like I’m
going to pee when I’m actually not. But regardless, I usually like the feeling and enjoy it. It really is an acquired taste and sometimes the
truth of the matter is that the dick is too big not to hurt. Lots of lube is an absolute must. The first attempts at sticking his dick inside of you
must be extremely slow, gentle, and gradual. Your asshole is much tighter than your vagina and stretches at a slower rate. After you feel your
ass loosening up a bit from his slow, gentle, and gradual thrusts, tell him when he can go harder. But the first moments may be
uncomfortable. As I said, it’s an acquired taste. But I definitely encourage you to try it. If you find the pain to be unbearable, just switch back
to vaginal sex.
Regarding the stigma of being known as the girl who has anal sex— what you choose to do is nobody else’s business. It is necessary that you
voice your concerns to your partner. Don’t do anything until you’ve gained his trust. I have friends who prefer not to have anal sex. It’s a
personal decision and if I followed my friends’ personal decisions, then I would be missing out on a lot. Make your own opinion the loudest
voice inside your head. As I always preach, sex should be about sex. We are living in a culture that is slowly but surely making it more and
more socially acceptable for women to be sexually liberal. Have anal sex simply because you want to and do it with a trustworthy fellow.
Peer pressure only exists if you acknowledge it. Again, if you choose the right guy who is discrete about it, then you shouldn’t be concerned.
Risks:
In order to explain the risks, let’s formally discuss the physical structure of your ass. What I am about to say isn’t going to be sexually
arousing…in fact it’s probably going to gross you out. I am going to explain how carelessness can tear your asshole apart and what the
effects will be. But both partners need to know this, so please proceed. In case you’ve ever watched Talk Sex With Sue (Johanson), she is an
expert. I have referred to her teachings in times of need, and I will now pass them on to you. Remember, AS LONG AS THE GUY
DOESN’T TREAT THE GIRL’S ASS LIKE A HOLE IN A BLOW-UP DOLL, THERE IS NOTHING TO WORRY ABOUT. At the lower
end of the bowel, there are two specific circular groupings of muscles called sphincters. One stands above the other with an inch or two in
between them. These open and close tightly and are responsible for keeping the feces/gas from coming through. The mucous membrane
lining of the rectum is not as thick as the vaginal lining, so your anal passageway is more susceptible to tearing and will take much longer
than the vagina to heal itself. It is also worth noting that feces/gas pass through on a regular basis with the help of your sphincters. So when
your sphincters open, the bacteria from the feces/gas can easily infect any tear. Tears also make you more prone to catching STDs and STIs.
If a fissure (a.k.a tear in your rectum) is big enough, you may need surgery followed by an uncomfortable recovery. A tear that is neglected
can expand out through your bowel wall and create a current that will flow into your vagina. What I am describing is called a “fistula” which
basically enables feces to flow from the rectum into the vagina and out. Disgusting, right? The moral of this graphic description is to be
smart about anal sex. No girl wants her ass torn apart, and no guy wants to be deemed responsible and have to pay the medical bills.
