Dear Stepdaddy - the 2011 Annual

by Stepdaddy

Copyright© 2011 by Stepdaddy

Erotica Sex Story: Award-winning letters to the "Dear Stepdaddy" hebephilic advice column from the year 2011. A wide variety of separate situations, and hence a wide variety of codes. So don't be turned off by one or two -- they likely appear in only one letter. Teen-aged girls, their Uncles, Teachers, Fathers and "Mentors" all write to the column for advice. Start the New Year off right with this "year in review" -- and then get busy writing your own letters to "Dear Stepdaddy" for 2012!

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Ma/mt   Consensual   Reluctant   Heterosexual   Shemale   Humor   Incest   Father   Daughter   Uncle   Niece   Spanking   First   Oral Sex   Sex Toys   Pregnancy   Teacher/Student   Babysitter   .


Many readers may be unaware that Stepdaddy's blog consists primarily of my "Dear Stepdaddy" advice column, a sort of hebephilic Ann Landers, if you will. Of course, these are all just fantasies, mine and my correspondents'. Here at year end, 2011, I am compiling this year's collection into the first of what I hope will be many "annuals". These have been edited lightly, and in particular some numbers have been corrected.

At the end of this work, please join me again to learn how you can contribute to and collaborate with the "Dear Stepdaddy" column, for the enjoyment of all.

Also note that where Stepdaddy lives in the U.S., "middle school" encompasses the seventh, eighth, and sometimes ninth grades. Students normally turn fourteen in the eighth grade.

January 29, 2011 – Dear Stepdaddy: Tattoo Hullabaloo

Dear Stepdaddy,

I've been modeling my life on your writings ever since my daughter turned fourteen. As you might imagine, my entire existence now revolves around my little princess!

Now the precocious eighth grader is begging me to sign a consent form so that she can get a tattoo. I know that tattoos are all the rage, but don't you think they'll go out of style soon, leaving my little Sweetpea regretting the choice? What should I do?

-- Wrapped Around Her Finger

Dear Wrapped,

I agree with you about this surprisingly long-lived fad: it has to end soon. Yes, it is very hot to see a young little teenie-bopper wearing a tattoo in a sexy location, but this has gone far enough. Not only do many eighth-graders sport them (yummy!), but so do a lot of eighth-graders' moms (yuck!).

I myself have been faced with this decision. My own daughter begged me to let her get a special tattoo, and her specific idea was certainly a rod-stiffener.

Sure, it would have looked totally cute at fourteen, but then I thought eight or ten years into the future. By then, my little cupcake will be all grown up, and in graduate school, if my hopes for her pan out. What if she realizes then that the favor of her faculty advisor is worth currying, and she arranges to allow the forty-year old lesbian to dine between her thighs upon her clean-shaven muffin?

The more I thought, meditated, and masturbated about it, the more I realized that this busybody feminist academic, admittedly mythical and yet so vivid in my minds' eye, might cause both my daughter and me all sorts of trouble.

Sure, she'd love the tattoo, and would probably go cross-eyed over the course of the semester, staring down the length of her own nose at it throughout her lengthy and talented cunnilingual sessions as she worshipped between my daughter's tender thighs. But as the semester approached its conclusion, and she imagined my little girl coming home to see me over the holiday, I figure the jealous old dyke would find some way to either blackmail my daughter or to get me indicted, just because of a cute, clit-crowning tattoo, inked in so many years before, reading: "Daddy's Cum Dump."

I suggest instead you make the compromise we did: piercings. It's hip, it's sexy, and ultimately, they're removable. And although you may be disappointed that you didn't get to permanently brand your daughter, you'll enjoy countless hours twisting her nipple rings, chewing on her clit ring, and spanking her ass on the pretext that her labial rings are just too fucking slutty. And, if your daughter ever goes to graduate school, the horny muff-diving "womyns studies" professor she enslaves will have no idea that it is you she has to thank for her good fortune.

I always say, "Better safe than sorry."


February 2, 2011 – Dear Stepdaddy: A Question of Semantics

Dear Stepdaddy,

Is it "hebephilia" or "ephebophilia"? I've seen both in written sources. Which is more correct, and which sounds better to you?

--Scrabble Nuts

Dear Nuts,

Either term may be used to describe the sexual attraction (usually of a male) to a pubescent or post-pubescent adolescent (usually a girl).

I think that the more correct term is "ephebophilia," but both are used in scientific articles on the subject. I prefer to use "hebephilia" because it is more pronounceable and it sounds better to me.

But what REALLY sounds better to me, of course, is a detailed description of a light dusting of silky-soft, emergent pubic hairs, sprouting adorably above a fourteen-or-fifteen year old cutie's puffy biscuit.

Pebbly little nipples atop lemon-sized titlets, which harden and stiffen at the most embarrassing times!

A thirsty, middle-school womb, eager to accept, absorb, and convert Stepdaddy sperm, in joyful combination with the very first (or at least a very early) fertile ovum ever to take an expectant trek down one or the other of her newly-relevant fallopian tunnels.

And perhaps later, as she rests from the bout, semen trickling out of her junior-miss hole, her training bra rubbing across the beard-stubble abrasions that redden her young mammaries a tad uncomfortably, she will pop her bubblegum, complain to her mentor that "school is SOOOO boring," and ask me to explain ONE MORE TIME about adding mixed fractions.

That's what really sounds good to me. Thanks for your letter.


February 4, 2011 – Dear Stepdaddy: A Panty Problem

Dear Stepdaddy,

My eighth grade softball practice was canceled (Go Bobcats!), so I was home from school early yesterday. As I walked up the stairs I heard someone talking in my bedroom. I knew Gramps was visiting us from up north to get away from the snow, so I figured it must have been him.

The door was open and when I peeked inside – OMG – Gramps was lying on my bed, all naked, with his thingee in his hand and he was pumping it up and down and my panties were all over him. He was holding one pair to his face -- eww! -- they were the ones I'd thrown in the laundry that morning! His accented voice came right through the crotch part of the undies: "Oy, dalink. Suck it dalink. Put your mouth on it and suck it. Oy, da panties. Da panties."

I was going to run away but I couldn't stop watching because I was wondering what it would be like to touch that stiff thing (and I was wondering what was with all the underwear, anyway?) and I even got that nice feeling in between my legs and I wanted to touch myself but I was afraid to. But when he made a lot of noise and the white stuff came dribbling out, I ran downstairs.

Gramps is going to be here for another week and I don't know what to do. I need some advice Stepdaddy.

-- Moist in Miami

Dear Moist,

First, you should know that what your Gramps is doing with your undies is completely understandable. I thank you for sending along a pair of your freshly-worn panties with this letter; if you wish to know how they were put to use, please see the Stepdaddy blog post "Ambrosia" of January 17, 2011, or read my poem "Laundry Day" from The Treasury of Stepdaddy Verse.

Your adorable little white panties, especially when scented (and flavored) by your own junior-high squishy bits, are an excellent accompaniment to a man's self-pleasure, be it mine or your Gramps'.

Now to the advice:

It is likely that your Gramps is already an avid reader of this column, so he may very well recognize the events in your letter and take the initiative himself. (Gramps, if you're reading this, you know what to do!)

Otherwise, you'll have to take things – and his "thingee" – into your own hands.

I suggest you put on a short skirt and white cotton undies, and leave the house as though you are walking to school. Hide somewhere nearby, so you can see when your parents have left for work (feel free to touch your special place through your panties while you wait – this will give you courage for what you must do next, and it will also make your "secret weapon" that much more irresistible).

Sneak back into the house and find him. No matter how he reacts when he first sees you, simply reach under your skirt, pull down and off your panties, and present them to your probably-speechless Gramps. Try to get them as close to his nose as possible right away. Then ask him: "Gramps, will you call the school and tell them I'll be sick at home today?"

That is what you should do to solve your dilemma.


February 5, 2011 – Dear Stepdaddy: Forms of Address


Dear Stepdaddy,

I'm an 18-year old college freshman girl and at this time an undeclared major. I'm just not sure what I want to do with my life.

So last November I met this cute guy at a Starbucks and we hit it off. He happens to be 42 yet we still really connected.

So lately during sex, he wants me to call him Daddy. I know he's old enough to be my dad but it just seems really weird. If I call him Daddy would I be betraying my real daddy? One of my gfs said my bf looks kind of like my daddy. I don't see it.

I'm just so confused. Do I just have cold feet and so I should go with my bf's idea in calling him Daddy during intercourse, or is this a sign that I should break up with him? Is there some other aspect of this I'm not thinking of?

--Bewildered in Baton Rogue

Dear Bewildered,

Candace, is that you? You know I gave the choice of either "Daddy" or "Sir!"

Just kidding Bewildered, I know you're not my Candace, as none of Stepdaddy's chicklets would ever be in your unfortunate situation – confused and neglected.

I can easily read between the lines and tell that you actually call this gentleman by his first name, not only in daily life but also during sex! Clearly, he is not a reader of Stepdaddy!

My young ladies always call me by a respectful form of address: Daddy (for daughters, stepdaughters, foster daughters, and many others for whom I deem it appropriate), Mr. ________ (for pupils, babysitters, neighborhood sweeties, and papergirls), and, in particular cases, Uncle, Reverend, Coach or Boss. They address me in these terms all the time, but especially during a spanking session or when I am roundly fucking them.

How do I know your relationship is on the wrong track? Well, in addition to your resistance to calling him Daddy (despite your strong instinctual desire to do so), you refer to him as your "bf" and you speak of "intercourse."

"Bf", I can only assume, is some shorthand you youngsters use to indicate "boyfriend." That's your first problem. He should have handled this from the start in a manner such that you would not even think of him as your boyfriend. By now, in your mind he should be your Daddy, your Mentor, your Master, your Teacher, or even your Cock Lord. "Boyfriend" indeed!

And "intercourse". Please. Acts of sexual congress with the sort of man you need to be with should be to you "my punishment", "my attitude adjustment", "my lesson", "my breeding", "my workout", "my treatment", "my training", "being put through my paces", "my medicine", "having some respect fucked into me" or the like. Intercourse! You poor thing.

As to your proximate predicament, you should either start calling him (and thinking of him ) as Daddy all the time, or get rid of this guy and find a more Stepdaddy-like mentor (your professors might be a good place to look).

As to your underlying problem ("I'm just not sure what I want to do with my life"), that much is obvious. What you want to do is quit school, go back home, and have your real Daddy fuck some sense (and maybe a baby or two) into you.


February 6, 2011 – Dear Stepdaddy : Unnatural Laws

Dear Stepdaddy:

Considering that the age of consent laws in most states are sixteen years old or older, why is that so many fourteen- or fifteen-year old girls have budding titties, widening hips, jutting bottoms, and so forth?

-- Rule Follower in Rockford

Dear Follower:

So we will want to fuck them, of course, as Nature intends for them at that age.


February 13, 2011 – Dear Stepdaddy: Staring Uncle

Dear Stepdaddy,

I'm a 16 year old girl. Lately when my uncle is over at my house I've secretly caught him peeking down my top or staring at my butt. The first couple of times I thought I had a stain or something but I don't think so anymore.

My uncle's stare is the same kind of stare all the boys at school have when me and my girlfriends walk by. We like that the boys think we're hot looking and probably have sexy thoughts about us so it's weird knowing my uncle has sexy thoughts about me. At first I was creeped out by the idea but now I'm not so sure because I also feel flattered that my uncle thinks I look hot.

Should I tell him I noticed that he looks at me or should I just be quiet and let him look without realizing that I know about it?

-- Confused in Concord

Dear Confused,

I am so glad you sought out my advice about this: for a girl, the age of sixteen can be an exciting, confusing and potentially hazardous time.

You mention how the boys in your school like to stare at you and your friends as you walk past them, and suppose they are having "sexy thoughts". That is a mild way to put it. What they are having are hormone-fueled lustful reactions -- "thought" barely enters into it. If you could only read their minds, you'd find them filled with disjointed, confused, and often mistaken imagery, and if you were ever unfortunate enough to allow one of these boys to have his way with you, the result would be a disjointed, confused, and mistaken effort on his inexperienced part.

Luckily for you, you have an uncle who often visits your home. If you could read his mind when he is checking out your titties and bottom (and also checking out your lips, your legs, your pelvic arch, and your nubile hip-to-waist ratio), you'd find it completely unconfused and coherent. You'd find in it clear imagery of how he would like to take his pleasure, in a masterful fashion, from your hungry body.

Now, on to your question as to what you should do. You ask if you should "tell him [you] noticed that he looks at [you]." A good rule of thumb in life is "show, don't tell".

Show him you've noticed by changing your outfit after he arrives, into a looser top (no bra), or into tights (no panties underneath) or, weather permitting, into a bathing suit. The more regularly and obviously you do this, the clearer it will become to your uncle that you've noticed his noticing.

If you're doing it right, you'll find yourself reacting, and not just by being flattered. You'll feel your nipples get hard around him, and your girl-place get warm and moist. Whenever you succeed in reaching these good feelings, reward yourself by asking your uncle if you can sit in his lap, or if he'll give you a massage.

It shouldn't take long before your uncle starts to guide you along the path to true fulfillment. And unlike those boys at school, you can trust him – after all, he is your uncle.

I've sent along by regular post my bank account's wire instructions should your uncle ever wish to thank me properly for helping you out with this.


February 20, 2011 – Dear Stepdaddy: Tell Me Why

Dear Stepdaddy,

What could ever convince a 34-year old male gymnastics coach, with a long and notable career (including, according to police blotter in our local paper, a first alternate position for the 2000 Sydney Olympics) that he ought to have sex with one of his adolescent athletes?

-- Outraged in Oregon

Dear Outraged,

That's easy: an opportunity and the belief that he might get away with it.

- SD

P.S. to other gymnastics coaches, Sunday School teachers, etc. – to play it safe, read the entire corpus of Stepdaddy stories as part of your planning and risk management process!

March 5, 2011 – Dear Stepdaddy: Boundaries?

Dear Stepdaddy,

Is there a general rule for what is inappropriate activity with an adorable adolescent girl?

-- Careful with Boundaries

Dear Careful,

Yes – it is inappropriate for you to fuck the little crumpet before I do, if it can be helped. Just kidding, have at it, Careful. I try to limit my activities to those which cause no permanent physical harm – unless carrying my squirming bastard between her just-broadening hips for nine months and going through labor that first time at the age of fourteen can be considered "physical harm." Some things just happen.


March 13, 2011 – Dear Stepdaddy: Sissy Boys?

Dear Stepdaddy:

Can I be a hebephile and like cross-dressing boys?

--My Cock is Confused

Dear Confused,

Absolutely! For any readers who doubt this, let me draw you a picture, based upon many of my own experiences in this regard.

There is nothing wrong with a cross-dressing boy, especially not with a cute, smooth Asian (let's say Thai), about fourteen, who looks like a delicate, and very feminine, adolescent girl.

This look is further underscored by the sailor-style school-girl uniform "she" has on ... or more precisely, its remnants, whatever hasn't been torn, pulled off, or disheveled completely by the make-out and heavy-petting session that has brought you to your current position, to wit:

You are reclining, your very pleased prick buried deep in "her" boy-pussy, as "she" rides up and down your imbedded pinion luxuriantly and needfully. "Her" otherwise complete femininity is belied by, but the eroticism of the scene is hugely magnified by, only one discordant feature. The front of her blue-pleated sailor-skirt is draped over "her" very stiff, prematurely-large, hairless or cleanly shaved prick, which protrudes out over your naked torso a seemingly-impossible six inches, cantilevered in "her" arousal from "her" petite, golden-hued eighty-pound frame.

"She" doesn't touch "herself" to keep hard -- "she" doesn't need to. Sure, you occasionally give that clit-stick a teasing pull or two as "her" clutching rectal sheath almost-magically milks your manhood, virtually sucking your balls out through the head of your cock, as though "she" is suffering from some kind of colonic sperm-starvation.

No, "her" disproportionate boy-clit doesn't require any manual stimulation from you or from the sissyboy "herself" -- despite the fact that again and again, you find you can't resist playing with it. You see, your young companion is plenty aroused from the pleasure the head of your cock is providing, as it rubs, bumps, and bludgeons itself against "her" deep-seated "G-spot", which in "her" case serves double-duty as a stimulated prostate gland.

"Her" dark, almond-shaped eyes widen whenever you jam up into "her" girlish bottom with extra urgency. Within a few minutes, this stimulation alone is sufficient to bring "her" off in teenaged quantities, and just in time, too, for as "her" copious white spew spatters across your chest and belly, and as "her" underage ass-channel seizes down on your thick penis in a temporary death-grip, your own balls collapse in ecstasy and blast a load like you haven't produced in years deep up into "her" welcoming guts.

Exhausted, "she" collapses upon you, smearing "her" own spooge between your two chests -- "hers" perfectly smooth, albeit with artificial-hormone-induced nubbins, yours perhaps hairy. As you both try to catch your breath, and as "her" ass flutters around your already re-stiffening shaft, "she" whispers to you in broken, pidgin English, learned during "her" mere few weeks' experience so far in the Bangkok "tourist trade."

"Pease, meester ... you buy me for whole week, okay?"

Your prick casts its vote, swelling again to full strength, and in obedience to its demands, you begin to roll your young companion over for what will prove to be a decidedly un-tender doggy-style round.

Now, Confused, are you confused anymore?


April 9, 2011 –Dear Stepdaddy: A Bone to Pick

Dear Stepdaddy,

I have a bone to pick with you! I have been reading your stories and columns for a while now, and in fact I used the trick of "accidentally" leaving a couple of your story files open on the computer for my Dad to find as part of my successful mission to get him to take my fourteen-year old virginity last summer.

My issue with you is the advice you gave to "Wrapped Around Her Finger" back in January. His daughter wanted a sexy tattoo over her pussy, and you talked him out of it, telling him to instead go with piercings.

Thanks a bunch! I had finally talked my Daddy into letting me get a "Property of Daddy" tattoo right above my clit when he saw your column and changed his mind. Yes, like you recommended, we went the piercings route, and yes, just as you suggested, he has enjoyed twisting my nipple rings, chewing on my clit ring, and spanking my ass on the "pretext that my labial rings are just too damn slutty."

But I want a tattoo! The future scenario you describe, in which someday my graduate school advisor in womyn's studies will frown upon it as she feasts upon my cunt all semester, and then somehow turns this knowledge against me and my Dad, just doesn't apply in our case.

Any and every woman who eats my pussy will be my submissive slave, that's the deal. Just ask Miss Reynolds, the pretty vice-principal for my ninth grade. She's known better than to ask any questions about my multiplying pubic piercings – she wouldn't dare risk getting cut off from the pleasure of servicing me after school.

So there you have it, I am going to get a pussy tattoo, so given that fact, do you have any creative suggestions?

-- Sassy in Sacramento

Dear Sassy,

I think the first thing you need (and want) is to be put over Stepdaddy's lap for a sound spanking. But if you really want a tattoo, make it practical and versatile. I suggest simple verbiage, with suitable scrolling and decoration. The permanent portion should read:

... if you can read this, I'd better be getting that...

Have the artist put rectangular boxes both above and below this inscription. You, meanwhile, can practice some calligraphy (in a mirror) and get a goodly supply of fine-tip Sharpies in the colors of your choice. Then, you will be able to "customize" your tattoo to fit the situation at hand by writing in appropriate addressees for the first phrase and appropriate indirect objects for the second phrase within these rectangular blanks.

Let me give you a few examples:

Daddy ... if you can read this, I'd better be getting that ... car.

Coach ... if you can read this, I'd better be getting that ... starter's position

Mrs. Pelligrew ... if you can read this, I'd better be getting that ... A

Later on in life, parings such as


can keep it fresh and profitable.

Good luck!


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