Dear Stepdaddy -- the 2012 Annual

by Stepdaddy

Caution: This Humor Sex Story contains strong sexual content, including Ma/ft, Fa/ft, Consensual, Reluctant, True Story, Humor, Incest, Father, Daughter, Uncle, Niece, Spanking, First, Oral Sex, Anal Sex, Bestiality, Pregnancy, Prostitution, .

Desc: Humor Sex Story: A collection of the finest letters to the "Dear Stepdaddy" advice column and blog from 2012, and the learned responses they received.


As many readers know, Stepdaddy's blog consists primarily of the "Dear Stepdaddy" advice column, a sort of hebephilic Ann Landers, if you will. Of course, these are all just the fantasies of my correspondents, and my fictionalized responses.

This collection takes its place as the second Annual of these letters, the second of what I hope will be many more in the years to come. However, that depends upon you. Please send me your "fictionalized" letters, to fuel the flame in 2013.

Of special note, be aware in the below that where Stepdaddy lives, "junior high" or "middle school" encompasses the seventh, eighth, and sometimes ninth grades. Students normally turn fourteen before or in the eighth grade. Stepdaddy uses the term "hebephilia" to refer to an attraction to teenaged girls, from fourteen on up – but not too far up.

Dear Stepdaddy: Of Beasts and Bonds

Dear Stepdaddy,

Is there any place for bestiality or bondage in hebephilia?

--Softball Pitcher

Dear Pitcher,

You might as well be asking is there any place for nipple-twisting, or any place for pube-plucking!

Of course there's a place for bestiality and bondage, separately or in conjunction. In my foster-daughter's case, that place is the living room when no one else but she and I (and Duke, my Great Dane) are at home.

More precisely, that place is the padded settee she gets draped across, her thin wrists cuffed to the settee's legs at one end, her skinny young ankles spread and bound with soft rope to the its legs at the other. She looks like a jockey riding down the home stretch in this posture -- well, except that she makes my dick hard.

That is the place where, with her eighth-grade cheerleading skirt thrown up over her back (she always removes her cheer panties on the drive home from practice, so that I can finger her enroute), the adorably elfin fourteen-year old takes repeated breedings from the one-hundred-fifty pound Great Dane.

Often, I'll kneel in front of her so she can gag on my mercilessly-imbedded cock, while cupfulls of scalding canine cum are hosing her uterus, but only once they're tied and Duke has stepped over his bitch to plug her with his knot for twenty or thirty minutes, ass-to-tail. I don't like to use her face while he's still mounted over her back, panting and growling and slobbering, because being face-to-face with him is hardly my cup of tea. After all, she's the bondage-slut dog-whore, not me!


Dear Stepdaddy -- Turning the Tables

Dear Stepdaddy:

Are you still writing your advice column?

-- Just Wondering

Dear Wondering:

Your question is indeed just. Like any procrastinator, I would like to claim that I have been very busy lately, and it is for that reason you have seen little of this column of late. However, that would not be accurate -- well, I have in fact been quite busy, but that is not the cause of the paucity of my postings.

The fact of the matter is that I have received no letters seeking advice in quite some time. As evidence of that, notice that I am forced to dragoon your simple inquiry into an excuse to post.

My advice is most helpful (and most entertaining for all) when it is offered in response to an actual reader request, rather than relying on my speculations (educated and accurate as these may be) as to what advice my readers need. Clearly, the spicier, dicier, or more outlandish the correspondent's dilemma, the more useful and fun is my proffered "wisdom."

In a viscous cycle, this column seems to get the most mail after I have posted a story, but I tend to get motivated to write and post stories by the receipt of good "Dear Stepdaddy" letters. Ironic, ain't it?

So how about we turn the tables? I am taking a risk here, in that my stratagem might fail to elicit any response, so please, gentle readers all, give serious consideration to helping me out here, by writing to this column with your advice for me.

I am currently teaching a Sunday School class. You will no doubt be unsurprised to learn that as we volunteers sorted out class assignments, I found one reason after another to reject both elementary aged classes and adult groups. Wouldn't you know it; I somehow ended up with a mixed class of seventh- and eighth-graders!

So here is the dilemma for which I seek your advice. The term is only twelve weeks, and I only see my charges on Sunday mornings. However, this summer, I will also accompany this group (as a chaperone!) to a week-long sleep-away church camp. Naturally, with only a week of overnights, I will not want to squander any potential coital time with belated seduction and preparatory manipulation.

I have to decide which girl in my class to "prepare" over the next 12 Sundays so that come the first night at camp, I can have her begging for Stepdaddy cock as though it were her own idea.

Here are the candidates:

1) Melissa – an all American girl, blonde and blue, eighth grade cheerleader, confident and popular. Most likely a virgin, but I don't doubt with her looks and popularity, she's had "boyfriends" and at least "made out" a few times. Needs a "manfriend" like Yours Truly to take her off the pedestal mere boys have placed her on, for her own good, of course.

2) Chloe – tough girl act, but all show, I suspect. Single mother home, got a bit of a Goth attitude, with piercings, hair dyed very black, a smart mouth that is often in a practiced snarl but that would look lovely around my cockhead. Trying too hard to come across as a sluttish badass – but in hanging around the sort of third-string social rejects who often join this sort of clique in middle school, she is probably also a virgin. In short, she needs some respect fucked into her to get her life onto a more positive track.

3) Edith – shy half-Asian girl who is fourteen but could pass for twelve given the girlish clothes she usually wears. Honey brown hair, hazel eyes with a hint of an almond slant. Very meek, petite, and innocent: definitely a virgin. I have spent some libidinous moments imagining how sparse and silky her dainty little patch of newly-fledging pubes must be. She could benefit from being coaxed out of her shell by an unfairly-large Stepdaddy cock being pressed into her sweet little oyster.

So please, readers all, write with your recommendations and justifications, as well as any suggestions as to the approach I should take with your recommended girl.

I know many will suggest I take down all three, and believe me I would like to, but let's be realistic. I only have time and opportunity to chase down one between now and church camp.

Lastly, I am definitely open for business to address any of your personal inquiries and sexual conundrums, so send those along, too!


Update on my Request

Dear readers of "Dear Stepdaddy":

I have been gratified by the responses my plea for advice in my "Turning the Tables" post has elicited. Readers have written to voice and justify their preferences and many have added delightful analyses of their personal favorite's likely characteristics, attitudes, susceptibilities, and even some suggested approaches that I, as a Sunday School teacher bent on sin, might take.

Please keep them coming, and provide all the detail you like. Additionally, if you give me a return email, I may seek further clarification from you.

My intent is to edit and publish this collective wisdom in a future post.

By the way, my actual effort with one of these girls is already underway, to be recounted after Camp.


[Editor's note: as of the posting of this 2012 Annual, Stepdaddy is still accepting your advice on this subject. The collection of reader wisdom will be published as a story soon, with full anonymity for contributors unless you direct otherwise. My actual exploits will of course will also be included.]

Dear Stepdaddy: An Anal Puzzler

Dear Stepdaddy,

I am sixteen years old and a bit of a late starter, at least from what I read in your column and stories. I didn't lose my cherry until last year, when my Uncle Rob decided I needed some proper training. I didn't realize how far behind my classmates I was falling.

First, he taught me to suck his cock. I didn't even think I wanted to learn that, but now I love it when I make him groan. Since he lives right next door, I was getting plenty of practice (he taught me to always swallow), and one evening when I was over at his place (my parents were out at a fancy dinner), Uncle Rob announced that I was ready. He said that since I now clearly enjoyed giving blowjobs, he could finally reward me by fucking me. I think he took some Viagra or something that first night, because he fucked my virgin pussy five times. Boy was I sore – and hooked!

It wasn't long until he started talking about fucking me in the ass. Now, I never thought I'd ever let anybody do that to me, and if he had ever discussed it in a normal conversation, I would have told him so in no uncertain terms. Unfortunately, I never really got a chance to test that, since he invariably brought it up while he was slow-stroking my cunt with his big uncle-dick.

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