Fred Requests a woman's point of view to help him understand. Then Maye weighs in with good memories and advice.
By BOSTON FICTION WRITER & MayhemLass Listen to the Podcast at How To Sex.
Fred’s Question
Dear BFW;
I've
never tried anal sex before. It never appealed to me. Actually, I never
have given it much thought until I perused the anal sex category here
at Literotica and found it so popular.
I
am a bit embarrassed to admit it, but I have never even had sex doggie
style either. Yes, I realize that doggie style sex is an overwhelming
favorite for hordes of people but not for me. It is not that I did not
try having sex doggie style, it just did not work for me; my cock did
not reach far enough for me to feel like I was fucking her. I mean,
really fucking her. Okay, it reached but it would not go in far enough
for me to feel that feeling of deep and satisfying penetration. It felt
weird. I mean, I do not have a small cock. My cock is a little bigger
than average at 7". Yeah, she seemed to enjoy it, but I was not
receiving the same feeling that I receive when doing it missionary style
and being able to really pound her.
"Sorry, Honey, scoot down so that your head doesn't bang the wall."
Moreover,
although all the women who I have ever been with were clean, having
just showered, shaved, douched, and flossed, whenever I tried having sex
with them doggie style, I always received an aroma of excrement, which
is a total turn off. I mean, I really do not want to smell shit when I
am boning someone, and I am not even having sex with them anally; I am
just trying to do it doggie style. Yet, when you start pounding away,
pumping your pelvic area against her hips, you are going to get a whiff
of poopies. And even if she is the most beautiful chick, that is gross.
"Geez, Beyonce, what the Hell did you eat last night? You smell like a 3-day-old Taco Bell."
I remember growing up and that was one of the worse ranks you could say to someone about their mother.
"Shut up Carl! Your mother takes it up the ass."
Way
worse than saying that your mother wears combat boots, taking a cock up
the ass was a big insult. That is, until a Greek kid moved into the
neighborhood and we were playing; and then we started arguing over
something stupid and one kid said to the Greek kid.
"You mother takes it up the ass."
The
Greek kid, Nick, I think his name was, shrugged and walked away
because, apparently, she did take it up the ass. He probably thought the
kid was complimenting his mother instead of insulting her.
I
remember that movie back in the late '70's, Midnight Express with Billy
Hayes. He played a college student who went through Turkey hoping to
score some drugs, Hashish, and deliver them back to the United States,
only he was caught. Boy, those Turks fucked everybody up the ass; it did
not matter if you were a man or a woman. What did he call Turkey, a
country of pigs? Anyway, any time you dropped anything in that country,
you were best just to walk away from it and pretend that it was not
yours rather than to bend over and pick it up only to find a Turkish
cock up your ass.
"Fred, Is that your money clip?"
"Hasad, I don't know who that money clip belongs to but it is not mine."
"It has your name engraved on it, Fred."
"Hey, Hasad, do you think that I am the only person in Turkey named Freddie?"
"Yes."
"Okay Hasad, then, kick it over here and I'll lie on the ground with my ass to the pavement to pick it up."
Anyway,
call me ignorant and I am sure that I will piss off a lot of people who
are into anal sex but I always thought of anal sex as a gay thing or as
a Greek thing and never as a another choice selection to my sexual
menu.
"Honey, can I fuck you up the ass tonight?"
"Gee, Sweetie, wouldn't you rather have a blow job?"
"Okay, Honey."
Now
that I think of it, that movie with Burt Reynolds, Deliverance, I can
hear the banjo music, now, showed those mountain men fucking anything
that moved up the ass.
"Look, Darryl, a deer. Shoot it."
"Nah, let's track it and catch it. Then, we'll fuck it up the ass before we kill it and bring the meat home to Maw."
Oh,
and that scene in Quentin Tarantino's, Pulp Fiction where that
shopkeeper takes the black dude down the cellar and he calls his friend,
a cop, and they are both ready to bone this poor guy up the ass until
Butch Coolidge, Bruce Willis, saved his ass with a Samari's sword. Man
that was a violent movie. I betcha when Vincent Vega, John Travolta,
emerged from the bathroom after taking a shit, he would have preferred
taking it up the ass instead of being blown away with that sawed off
shotgun by Butch. They just don't make good family movies like that
don't the Eskimos like anal sex? Still, they have a reason; it is
fucking cold in those igloos. Who wants to take off your clothes to have
sex when it is so cold that the penguins are trying to get in bed with
you to keep warm? This way, the Eskimo women just inch down their seal
line pajama bottoms and bang go, you are getting off. How they rub noses
while having anal sex is something that I'd like to see, well...maybe
sex to me includes intercourse, of course, oral sex, and foreplay. I
can see Bubba in prison chomping at the bit not being able to wait until
he can get a good behavior pass to go out of his jail cell and to use
the computer in the library so that he can write me a nasty comment to
this story. Yet, you know, Bubba, if you hadn't been a criminal and dumb
enough to have been caught and have your sorry ass thrown in jail, then
you would not have to be boning some other convict up the ass while
sniffing their poopies. Matter of fact, once you are a free man and out
on the street, you cannot tell me that you would rather bone a hussy up
the ass instead of fucking them missionary style.
I
asked my girlfriend if she ever had anal sex and she said that she had
it once and did not care for it. Then, I asked my sister-in-law (I have
to be careful writing about my sister-in-law otherwise this piece can
easily become an incest, okay taboo piece, rather than an anal piece) if
she had anal sex and she said that she had. My sister-in-law was the
one who wanted me to have sex doggie style with her. She liked doing it
doggie style but I could not satisfy her that way. Hey, call me old
fashioned. To me, fucking someone up the ass is just sex and not making
love. I'd rather face the woman when I am making love to her; so that I
can kiss her and suck her tits. Maybe, that's it. I'm a tit man rather
than an ass man and it's rather hard trying to suck nipples when they
are way on the other side while you have your cock behind her instead of
in front of her where God intended Adam to bone Eve.
"Freddie,
you're hurting me and stretching my tits all out of shape trying to
pull them back to suck them while you are fucking me up the ass."
Now,
all the religious freaks will be coming out of the woodwork to make
nasty comments to this story. Hey, if you zealots are so full of
religion then you shouldn't be doing anal sex anyway. Doesn't the Bible
tell you that the only time you people are suppose to have sex is when
you are making babies?
"Honey, can I have sex with you, tonight?"
"I'm sorry, Jacob, but I am already pregnant. Give me 9 months and we'll have sex again, then."
Yeah,
try telling that to Moses. He had like 100 kids. He must have thought
he was a Mormon instead of a Jew and it was okay to have more than one
wife. Can you just see Mrs. Moses, now?
"Hey,
Moses. Why don't you bone me up the ass once in a while instead of
fucking me missionary style? I'm tired of having all these kids and with
you going up to the mountaintop waiting for Jesus to talk to you and
not being around to help change diapers. Moses! Where are you going with
all those animals? It's raining."
Okay,
for a brief period, 4 years, I was in the swinging lifestyle and I took
an unofficial survey of the women who I partied with (they call it
party with instead of saying had sex with) and everyone one of them said
that she has had anal sex. Yet, I did not find one woman who preferred
anal sex to penis to vagina intercourse. Now, that's an interesting
discovery, don't you think? Allow me to repeat that. There was not one
woman who would rather have anal sex to having regular penis to vagina
intercourse, not one.
"You look lovely tonight; I cannot wait to make love to you."
"Why
don't I just drop my panty and bend over. Then, you can fuck me up the
ass and we can continue our evening without all of the sexual
anticipation?"
"But, Honey, we are in the elevator."
"So, you say that like there is something wrong with that."
My
friend, Bill, who was a swinger, met this woman who wanted him to fuck
her up the ass. She had never had anal sex before and had always wanted
to try it. Her husband, the only other guy, apparently, like me who does
not like anal sex, would not accommodate her so Bill said, "Sure," he'd
fuck her up the ass. Only, and apparently, this woman did not know the
rules to anal sex. How could she? She never had it before. Well, before
attending this house party where the swingers gathered, the woman had
gone to dinner with her husband and had a big meal.
Well,
you guessed it. Bill was fucking her up the ass. Let me tell you about
Bill. He is one horny guy and can fuck better than anyone half his age
and he is 60. And he has this huge cock. Anyway, he's fucking this woman
up the ass and she is enjoying herself until, suddenly...Bill is
covered from his neck to his knees in her shit. She shit all over him
and all over the sheets. There was shit on the carpet and on the walls.
This woman must have been saving this shit up because it was everywhere.
There was so much shit. The woman was so embarrassed that she hauled
ass out of there with her husband and left poor Bill covered in shit. He
showered and returned to the room to help the hostess clean up the
mess. Now, that is a true story and you can ask Bill if you don't
believe me. Bill, get in here and tell the readers about that woman who
shit all over you when you were fucking her up the ass and that it is a
true story.
"It's true."
"Thanks, Bill."
Now,
let me end this story by writing that it was not my intention to pass
judgment or to insult or to criticize anyone's sexual lifestyle. I
embrace everyone's right to float their own boat so long as it is
between two consenting adults. Sorry, Darryl. I am only trying to
I ask you, what is the big deal about anal sex? I'd especially like to
hear a woman's point of view, a woman who not only enjoys it and looks
forward to it but also who prefers it to penis to vagina intercourse,
and one who is not Greek, Turkish or an Eskimo; l o l.
"Sorry,
Paris Hilton, you are just a slut and your opinion does not count.
What's that? You have a story to tell me that you want me to write about
you and Britney Spears and you want me to tell everyone the real reason
why Britney shaved her head? Okay. Well, I have to take off with Paris,
everyone. Ciao!"
How To Enjoy Anal Sex
One woman's suggestions.
MayhemLass answers Fred.
Judging
from the popularity of this category and the myriad of responses I
received, I have come to the conclusion that the misconceptions and
preconceived notions respecting anal sex are legendary. My impression is
for the most part that a lot of men want it and a lot of women are
horrified at the very thought. Generally, society has frowned on this
type of sex, as reflected in derogatory remarks such as "asshole".
Unfortunately, a lot of people are missing out on a great addition to
their sexual repertoire.
Before
I go any further, I want to VERY clearly urge anyone with ANY concerns
about their health to USE a condom. Even the gentlest anal sex can cause
tiny nicks and scratches that could easily conduct any organisms
straight into your body.
The
anus has a multitude of nerves and muscles which when stimulated
correctly, can provide enormous pleasure. Two sphincters are obvious
when a finger is inserted – the first which provides the 'pucker" with
which everyone is familiar, the other, about half an inch in. The first
is controlled by the individual consciously – thus you can tighten or
loosen it at will. The second is controlled by the part of the brain
that controls bodily functions such as heartbeat, breathing etc – i.e.
you cannot control its reactions directly. Proper and gentle
manipulation can be equally enjoyable for men – whose prostrate can be
stimulated from the insertion of a finger in the rectum – and for women,
whose G spot is readily massaged through this form of lovemaking.
I
would highly recommend that each individual familiarize themselves with
their own bodies, exploring their own fundaments first to gauge the
feeling and reactions that the insertion of a finger or object
an aficionado myself, and female, I thought it would be helpful to
address the issue and give my own suggestions/recommendations respecting
the introduction and enjoyment of this unique form of lovemaking. I
will deal with male penetration of a female's rectum as that is what I
can recommend and am familiar with.
Anal
sex is not something that should be introduced on a whim, nor thrust
upon someone who is unfamiliar with this very arousing form of
lovemaking. Ultimately, I believe that preparation and patience are the
two primary ingredients of a successful introduction to anal sex.
A
subtle yet honest form of behaviour modification works very well in
this regard. Introducing your lover by attempting to push a stiff penis
up a very small area unused to intrusions from that side of the body is a
guarantee of failure. Rather, start gently and carefully.
Preparing Her Desire
1.
First, begin with oral sex – an excellent starting point as you not
only have intimate access to the desired area but as your lover's
arousal increases, you are provided with the opportunity to gently and
subtly introduce a finger; for instance, just tickling the fundament as
your tongue takes care to keep her attention focused on the main event.
As your lover starts to peak, push your finger very gently within the
rim – do not go too deep or you will not only most likely derail her
orgasm (thus creating a very frustrated and angry lover), you will also
overstep the first steps to successful seduction.
Do
this frequently and often, allowing her to slowly get accustomed to the
feel of something tickling her anus, and in turn, linking an orgasm
with the sensation of a foreign object around her anus. Done correctly,
she will unconsciously begin to enjoy the extra stimulation provided by a
careful finger or a warm tongue.
My
strongest advice – DO NOT rush it! Most of us have been taught from a
young age that anything to do with the very natural functions conversant
with an anus are "dirty", that anything to do with the butt is "hands
off". So not only do most people have to deal with the startling reality
of accustoming themselves to something foreign in their anus – even
more importantly, they have to overcome societal imperatives and
Second, after your lover has become accustomed to – and learned to
enjoy – non-threatening anal play, slowly begin to increase the level of
your insertion. The anus does not self-lubricate, so unless your finger
is sufficiently lubricated with your partner's own juices, then use a
proper lubricant such as KY jelly or something similar. Providing oral
sex while gently thrusting your finger in and out of her anus after she
has learned to enjoy anal play is guaranteed to provide a very
satisfactory and intense orgasm – thus continuing your gentle behaviour
this stage, it can also be stimulating and encouraging to gently insert
a finger during intercourse. This can be done in a variety of
positions, the easiest being the female kneeling and the male
penetrating from the back. He then has easy access to her rectum and
although it can be tricky, the sensation engendered by double
penetration can be seductive and immensely exciting.
3.
Third. After a sufficient period of time has elapsed and your lover has
become accustomed to and enjoys her anus being stimulated, then you can
begin preparations for actual anal intercourse.
There
are some basic rules and preparation that I would highly recommend if
you want an enjoyable and satisfying experience with anal sex. I will
Be healthy – ensure there is plenty of fibre in your diet so that your
natural functions are normal and healthy. Some individuals prefer to
have an enema to ensure no fecal matter is present, but if your diet is
healthy and you have emptied your bowels, I do not believe this is
necessary.
• Have a recommended lubricant on hand, such as KY jelly.
•
Be conscious at all times of your lover's responses – being aware and
responsive to her reactions is crucial if both parties are to enjoy the
Next, it is probably most helpful to introduce anal sex when your lover
is already open, relaxed and aroused – i.e. don't START with it but
consider it the culmination of a sexy, fun and enthusiastic session of
lovemaking. This is also advised because due to matters of hygiene and
possible cross-contamination, it is highly recommended than the penis is
washed thoroughly and carefully with soap and water after anal sex. The
penis must be washed both to avoid any bacteria that might cause
infection in the penis, but also to avoid giving your lover any issues.
Preparing Her Anus
Thus, assuming that you are now ready to introduce the penis, I suggest the following:
1.
Lots of lubrication – particularly the first few times – play with your
partner's anus with lubricated fingers and warm tongue until the rectum
is relaxed and open. You can lubricate her rectum during play. Then,
ensure that your penis is similarly coated with a safe lubricant.
2.
Choosing a position which is comfortable for both of you – spoon
fashion works very well especially for the first few times as it gives
the woman more control – holding your penis firmly, push it gently – and
I mean gently, against the lubricated rectum. A lubricated anus
together with a lubricated penis almost guarantees that the spongy head
of the penis will slowly push in. JUST as you enter – STOP!
It
should be noted at this point, that the two sphincter muscles I
mentioned above now become relevant. The woman can help with the first
muscle by pushing out as if having a bowel movement - that flares the
anus open and gives egress to the penis. BUT, once the head of the penis
has entered, the man must stop and allow the inner sphincter muscles to
accommodate themselves to the intrusion. However, eager and open she
is, the woman cannot control that inner muscle and must wait for her
body to accommodate – forcing it at this point could damage and tear the
Let the woman take the initiative at this point. She has to accustom
herself to the feel of the penis in her butt – the sensation when first
experienced can feel quite uncomfortable, as if you need to have a bowel
movement. Allow her the time to relax both physically (given time, the
inner ring of muscles will loosen) and emotionally, to the feel of a
penis in her rectum. Allow her to take the lead, to indicate either
verbally or through her body that she is ready for you to push a little
more of your penis up. Again, Go Slow! As the penis is thrust up the
fundament, that ring of muscles will once again tighten; allow them the
time to loosen and relax as they accommodate the girth of the penis.
Once
the entire penis is inserted to the groin, relax and enjoy the
sensation before actually beginning to thrust. The woman can flex and
constrict the outer ring of muscles as she becomes used to the feel. By
slowing wiggling her bottom, she can control the rhythm and make the
decision when she wants her partner to push in or out.
4.
The feel of a penis up your rectum is immensely arousing once you have
been properly prepared. There is the physical reality that the anus has a
multitude of nerve endings and muscles that signal pleasure, the feel
of a thrusting penis against the G spot can induce a sensation unlike
any other (and can actually eventually lead to female ejaculation which
will be the subject of another essay) and then the emotional reality
that you are engaging in a "forbidden" pleasure can be in itself
stimulating and exciting.
Enjoying Anal
From
that point on, keeping hyper aware of your partner's response, you can
engage in an increasingly enthusiastic bout of anal intercourse. As the
intercourse continues, while the anus itself doesn't self-lubricate, the
sensation and intense pleasure will ensure that the woman's natural
lubrication together with the male's pre-cum mingle to form a very
satisfactory and slippery lubricant which adds to the pleasure and
allows intercourse to become more enthusiastic.
The
man, at this point, may want to reach around and stimulate the woman's
clitoris manually as it is quite common for women to require a little
only drawback to anal sex at this point occurs when the very exciting
session has culminated and both partners have orgasmed. While it is
tempting to loll in bed and enjoy the aftermath, it is crucial to wash
within a reasonably quick period after sex – both the male and the
female – to avoid the possibility of any infections.
I
would add at this point that once you and your partner have a little
more experience, some may prefer to use less lubricant or dispense with
it altogether. Many females such as myself prefer the rougher stimulus
provided by an unlubricated penis.
All in all, anal sex can be an exciting, arousing and fun addition to lovemaking.
By BOSTON FICTION WRITER & MayhemLass