These are questions sent to me per email. This is NOT me just randomly speaking/writing!!!!!!!!!!!!!!!!!!!!!!!!!!!!
So many people have written to me thinking the question below was about me; written by me. HELLO! Can't they READ!? DOH!
Q.
Next week I turn 40, a pretty major milestone. I have gone through my life so far
and failed to find a good man. All the men I have been involved with have mostly
turned out to be wasters or assholes. I look around at my friends and most are
happily married, or divorced and resettled with a partner. I am attractive, and
look young for my age (fitness instructor) but I just attract assholes. I am
depressed that I am as old as I am and have no reliable man in my life. It seems
to me that love is like a sale, if you turn up late all the good stuff is gone.
Most guys that try to hit on me are sleazy with no class; they would not make a
good partner. I guess what I am asking have I left it too late?
What about having kids? It feels like there is so little time left. I want to
come home to somebody; I don't want to end up 70 rocking away on my own by the
fire. I am too old to play games.
Birthday Barb
^ Madonna was hot at age 40 (& still is)
A.
40 is not old. Realize your main goal. Is it mostly having a child or a man? If it
is, there are many ways of getting pregnant to get that part underway. I am wondering
where you meet these sleazy assholes and how you dress. The environment you hang
out in and the way you dress tend to dictate what kind of men you attract. We have
the advantage of adjusting our selves according to what mood we are in. Example given,
if you are horny and just want a fuck, you can go out to a local bar wearing a short
shirt, low cut shirt and lots of make up to give off the "I’m in heat" vibe. The next
day, you could wear a long skirt, decent top and hang out in a cafe and give off a
very non sexual vibe. Be the partner you wish to attract; as in, if you want a sporty
guy, put yourself in a sporty atmosphere and so on. Finding a partner online is now
a common thing but you have to be very specific as to what you want. "Good looking
mature woman seeks grounded man to start a family with". No need to beat around the
bush when you feel you are running out of time. You can find love at any age, but
having kids may make you feel pressured by your bio clock. Trying to help you without
know where you live, what your financial status is (you could always buy an egg
later on) is a bit difficult but all in all, Birthdays tend to bring anyone over 30
down for a month or two but don't fret, many people have kids over 40 (or adopt) and
you can find love at every age. Who says it has to be a man that will make you happy
anyways? Chin up girl, you are still younger than Madonna.
Q.
Why are woman attracted to "bad boys"? What are they doing that attracts woman?
And what’s the best sexual position that a couple could use if the woman is trying
to get the deepest penetration?
Wee Little Willy
There is something irresistible about tough guys
A.
"Bad boys" don't go out of their way to be bad. They just don't give a shit. They
don't call and thank the woman for the great sex; they don't call when they say
they will call; they flirt when they are out on a date with other girls; they cheat,
lie, steal, ridicule and are just plain insensitive. They attract women with low
self esteem, who subconsciously feel they deserve to be treated badly (probably
because one or both of their parents, namely DAD, wasn't there or didn't give a fuck).
Doggy Style will make your tiny cock seem like an Anaconda if you can keep it hard, that is.
Q.
OMFG! I was going down on my girlfriend, and she was loving it, we where almost 20
minutes into it then she pulled my head and said "you gotta stop or I’m gonna shit on myself"!,
and I asked her if she was serious and she said she was, and we ended it, but I wanted to
know is could that really happen? How common is that?
Scared Shitless
A.
If you fuck/suck after having an Indian or Mexican dinner, it can happen.
She may have felt a fart coming on, but wasn't sure; but like she said, it's best that you
got the hell out of there when you did. I used to hang around with the British Soldiers in
Berlin (we all make mistakes) and I saw many guys shit themselves while and/or after drinking.
One of my friends told me that while fucking her drunken ex-boyfriend, she realized that
he shit himself and it got all over them and the bed. So alcohol usually contributes to
shitty situations. Avoid eating a few hours before sex so the bowels remain empty. And,
once you eat, a lot of your blood goes to your stomach for digestion, leaving your genitals
short on blood supply. You can get off better when you are tad hungry and all the blood can
engorge your naughty parts and there will be less, well, shit going on.
Q.
I'm in my early 30s and I've been messing around with this MILF for the last month,
we rarely use protection (I know it's not wise), really she's more like a GILF, because
she'll be 60 in a few months, but anyway she recently informed me that she might be pregnant,
there's a lot of problems that I have with her telling ME that, but one of the questions
that pops in my mind is, isn't she too old to conceive a child? I mean how likely is
that that a woman her age can get pregnant? Aren't her eggs to old?
Granny Shagger
A.
It's as about as likely as finding a snowball in hell. I think she may be enjoying a
bit of wishful thinking. Some Hollywood stars get pregnant around age 50 (Geena Davis
or Marcia Cross for example) but it's because they are artificially inseminated with
someone else’s egg fertilized by their man's sperm (or anyone's sperm). But this
procedure cost an enormous chunk of change that I doubt your horny GILF has stashed
in her coffee can. Once a woman stops having her period, she can't get pregnant anymore.
Have you ever asked her about her period? Has she ever mentioned it?
Don't panic just yet.
Q.
I need help! It’s been a year since my lady of 15
years dumped me and moved away. I can't move on! I’ve
tried everything! Riding my bike, making art, fixing up
my place going to shows drinking so much I fucked up
my liver (I’m sober now.) I can't sleep. Sometimes I'm up
for 3 days straight even though I exercise and take
sleeping pills. I’m a normal horny straight 36 year
old with modest needs but I can't seem to meet anybody
or get back in the saddle. My roomates gay and he offered
to set me but I’m hetro. It's been 15 years! I don't
how to talk to women! Dumb right. I’m confused, lonely
and really have lost my will to live. I love my ex
but she ain’t comin' back. Should I focus on work and
just chill? I know this column is usually for sex talk and
such but I was hoping you might have advice on
matters of the heart. How I can forget and just say "fuck it!"
and move on. I even started doing graffiti again just
to get a rush and a high but I’m to fuckin' to old
to be tagging!
Buried Alive in the Blues
A.
I feel you, but we ALL have to have our heart broken once
and to break someone's heart once in order for love to really work out.
We have all been there, where life doesn't seem like living anymore and no
one else can compare. The good news is, life does go one and time does
heal ALL wounds. Go on and have a good long cry and write down the good
things about her and the bad things about her then tear it up and throw
it away. Have a long
bath, long jog or walk and concentrate on making your body nice and healthy.
If you are happy in your job and where you live, your body and health should
be your main focus. If you hate your job and your home, maybe it's time for a
whole new life; a big change. Maybe you can move and start over. You are still
younger than Brad Pitt for fuck’s sake.
Stop wallowing in your self pity; we have ALL had this shit happen to us.
There are people all over the world with worse problems. Concentrate on the
positive things, like your age, health, freedom, etc.
Try not to listen to your gay room mate; most gays aren't specialists on giving
a hetero man pep talks on how to meet women! They prefer to try and convince
you to turn gay instead.
Don't try to forget her, just remember the good times and learn from any
mistakes that were made. You haven't really lost anyone unless they are dead.
Listen to some Frank Zappa and he will help you see it's not such a big deal,
particularly the song "Broken Hearts are for Assholes". This will shed some
light on the subject and help you move on with a smile.
Q.
I met a guy but I am being warned off by my friend for an odd reason. He is
cool smart and wicked hot. My friend said I shouldn't
go out with him because he is a redhead. She has told me a lot of rumors
about them. She says they are more promiscuous and that they have a wild
temper. She also said that they are extremely stubborn. She had a redhead
who was a good kisser but he was always in trouble and was
unpredictable and crazy. So far this guy has been pretty cool but what my
friend said is bothering me. He does have an interesting personality he is
either loud and entertaining or really quiet and it changes on a dime. I
like that about him but does it mean he’s insane? Or is my friend trying
to sabotage it? She
seems to like him as well.
Riding Little Red in the Hood
< I'd hit it
A.
She’s had “a” red head and now she’s an expert?
And since when is “Unpredictable” a bad trait? Do you want a boring, predictable
push over that follows a certain routine? Perhaps you should get a cat, not a man.
Red heads tend to have a temper due to all the harassment they get at school for
being different, but it's shallow and ignorant to say they are the more promiscuous
than blonde or brunette men. That's like saying Blondes are stupid.
I say try him out and tell your friend to calm the fuck down. Besides, all that pent
up frustration and temper comes out nicely in bed.
Q.
I’m a 60 yr. old single man but look about 15 to 20 years
younger; women I meet just assume I’m younger and I’m in the
entertainment field, should I tell them or just let them assume since I am in a
very vain business working or in social scenes? I use to own my own adult party
club for almost 20 years and it really was an alternative lifestyle for me since
naked was the code of dress and seeing sexual acts was the norm. I became so
jaded that only threesomes, two bi-women and me or anal sex seems to appeal to
me, I have been on the sidelines so to speak for a couple of years and about to
come into windfall of money! I feel that my sexual attitude will work against me
in trying to meet a single lady who is not into my sexual views. What is your
take on this?
Hef Wannabe
A.
You have two different issues to address here: your age and your sexual appetite.
Lets talk about your age first.
Even if you are chatting up women 20 or even 30 years younger than you, I
really doubt they would bring up the topic of age. Even a woman half your
age is at that point where women don't like talking about their age, so you
have that to your advantage. If they ask you your age, they know you will
be asking theirs and we don't want that so you are pretty much in the clear.
If they come straight out and ask, they are probably too ignorant to fuck anyways
and/or you could answer then with a snappy: "I am younger than Mick Jagger"
or "Old enough to know what I'm doing" or something coy like that.
Don't lie about your age, just answer the question with a question and a smile
on your face. Age doesn't matter. Charm and manners matter.
Secondly, many men would love threesomes, anal and to at least take part in one
orgy, but not all women have the same wild sexual views/aspirations that you have
being the naughty sex connoisseur that you are. You have seen and done it all
and have a tiny sexual attention span.
Women over 35 are usually at their sexual peak and open for experimenting.
I wouldn't exactly request a threesome on the first date; slowly show your freaky
side to new women you meet. No need to lie or pretend, just avoid telling them
everything up front (your erotic film career etc). Telling them you work in the
film industry would suffice at first.
At your age, using your wealth as an asset to lure women isn't tacky, it's just
reality; everyone uses what they have (looks/giant genitals/money/power) if they need to,
but showing all your cards too quickly could attract gold diggers, but if you don't mind,
then you really have nothing to worry about. Embrace your dirty old man era with gusto.
Q.
Just yesterday me and my boyfriend had sex (I was a virgin). We both had fun but there
were a few things I was wondering about. He didn't exactly "Pop my cherry" which
worries me slightly because it kinda hurt when he was going in but I didn’t bleed
and neither of us ended up cumming. We tried two different positions for about an hour.
He said from what he has read it only takes about 5 minutes. I may be new at this,
but that sounds like rush hour traffic to me.
Help,
Sandra Dee.
A.
Sometimes it takes women years to figure out how to orgasm. He may have not cum because
(1) He was nervous (2) He already wanked his dick raw before meeting up with you.
Popping one's cherry isn't a giant bloody production like you imagine.
The Hymen is a fold of mucous membrane up there that is easily ripped once you have
been penetrated. Some girls bleed and others don’t. Some break theirs if they shove
a tampon up there too violently.
You may want to buy some lube and use a tiny bit on your clam to ease entry pain.
It may hurt but the longer he spends on foreplay, the more he gets your juices flowing,
which makes penetration easier.
Before you can expect to cum with a partner, you have to figure out how to make yourself
cum, which I have written about many times already, just find my Ask Dr. Dot
archives online.
Q.
I’m 30yrs old and for the last few years I've had a craving for older women,
I think it’s more like a fetish, because I have relationships with women my age,
the older women are not just 5 or 10 years older their 20or 30 yrs older then me,
when I’m shopping for escorts 90% of the time I’m looking for milfs, one of my
questions over the phone are"whos the oldest one you have"?….I want to know where
can this have stemmed from?…and can this get out of control?…I mean the other
day I saw that a re-run of the Golden Girls was on, and stop and masturbated to it.
Gilf Hunter
A.
I call this the Harold and Maude syndrome. If you haven't seen this cult film yet,
please do. Perhaps when you were young, your Grandmother, or another older lady
Showed you love and more attention than anyone else; this could have sparked your
infatuation with Granny types. The fact that it's so taboo may be a turn on as
well as the fact that older women really know what they are doing and what
they want. I’ve always craved younger men; we all have our preferences. Maybe
it turns you on knowing older women get excited over young flesh? The possibilities
are endless and I don't think it's a negative fetish, I think its fine. Any
fetish that doesn't include children, animals, money, drugs or murder is fine in my eyes.