Introduction

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!

-SD

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!

--SD

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.

-SD

[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.

He would usually raise it while he was spoon-fucking me, his strong hands kneading at my tits as his cock slid in and out, his hips bumping up into my butt cheeks. "You know I'm going to be fucking you in this sweet ass soon, don't you?" All I could do at times like that was to moan and nod. "You want me to, don't you?" I'd hiss "yesss" and actually mean it! (at least at that moment). But what would really light my fuse was when he'd then say something like "And you know I can have it whether you want me to or not, because your body is mine, to use for my pleasure, right?" God, just the memory of my shamed agreement makes me wet, even as I write this!

Anyway, he eventually fucked my ass (yes, that's right, all three of my cherries were taken by my forty-year-old uncle, nothing saved for my future husband – or even my senior prom). It kind of burned, but later, the next day, I felt a little itchy in there and actually wanted some more.

Nowadays, I like it that he occasionally informs me that it's time I paid for my lip with my butthole, but I prefer vaginal sex by a long shot. But here's my question, Stepdaddy: I once asked him why he prefers anal sex to regular sex, and he told me that he doesn't! He prefers, he says, the "silky smooth grip of my teenaged twat to the tight, ring-like grip of my sphincter." His words. When I ask him, "If I like vaginal better, and you like vaginal better, how come you so often insists on anal?" he says it's because his "balls tell him I need it." What is he talking about?

-- Niece Piece

Dear Piece,

I can only assume that you read my stories and columns from print-outs made by your uncle. The website on which my writings are posted is off limits to persons of your age but, if your in loco parentis makes my thoughts available to you, all I can say is "truth wants to be free."

First of all, congratulations to both you and your uncle. In your case, you have been fortunate enough to have been broken in by someone who truly cares for you, and who will continue to care for you even if your sexual relationship comes to an end, as it probably will as you eventually get on with your adult life. Very few women have enjoyed that luxury. As for your uncle, well, after all the work (and risk) he has shouldered in order to give you this education, I am happy he has taken his rewards. I try very hard to never leave any cherry unshattered in my young protégés. After all, having made a substantial investment, I cannot be expected to leave any part of the prize basket to some future boyfriend or husband. Neither should any girl's uncle.

Because of his diligence, for the rest of your life, no matter who you are with or how much you love him, there is no orifice in your body that a future lover can penetrate without some part of your mind recalling "Uncle Rob owned that first."

So you see, for both your good and his, your Uncle Rob's "balls" occasionally remind him to renew his claim – his ownership – of your sweet little asshole. Meanwhile, it sounds like your own well-trained initiative is enough to keep his claims to your mouth and cunt up to date.

To answer the question you've asked your uncle, it appears that your Uncle Rob, like Stepdaddy, takes his responsibilities as mentor very seriously. Not every one of his decisions is made on the basis of his maximized, immediate pleasure, for example his tactile preference for slick pussy over clutching sphincter. Admirably, he takes a deeper, more philosophical pleasure in having done his duty – by ensuring that he does right by all of your slutty holes.

-SD

Dear Stepdaddy: Reprove to Improve

Dear Stepdaddy,

I am a regular reader of your columns and stories, and I often apply your methods in the training and "upbringing" of my fifteen-year-old foster daughter, Sam. When she gets a little too edgy, I am usually ready to give her the spankings she is asking for (and the follow-up daddy-fuck she is obviously angling for), leveraging both my own experience and the many pointers in your acclaimed Stepdaddy's Guide to Spanking.

My question is this: in addition to the delicious pre-heating a stern paddling can provide, are there any verbal (I almost said "oral"!) reprovals or chastisements that you can recommend, both to rein in an unruly teen and to set things into proper motion, if you know what I mean?

--Sore Hand in Sarasota

Dear Man with the Hand,

Thank-you for your letter. You can't know how gratifying it is to learn that my efforts have not been in vain, and that my personal vision – of making the world a better place for teenaged girls and the older men who would help them – has not gone completely unmarked.

As a reader of my works, you know that I enjoy my own role as a serial teen mentor immensely, and that I have authentic affection for my young mentees. That does not, however, mean that I try to be their "best friend", or speak to them as I would a peer. I care for them far too sincerely to treat them in such a well-intentioned but thoroughly misguided manner.

So, just as you do, I keep a hand ready to lovingly castigate my little honeys, with a vigor ranging from a playful swat to a blistering bare-butt beating. I am also prepared to twist a nipple or swiftly slide a hand past a waistband or under a skirt to rudely drive my unexpected finger into an impudent vagina or a sassy anus.

But, despite what my animalistic urges and my well-demonstrated verbal poverty might suggest, I also believe there is much a young lady can stand to gain through more cerebral interactions. The spoken word, the banter, the instruction – in short, the other kind of "intercourse" – can season the anticipation or execution of that sweet congress you and I both treasure.

One approach is what the kids call "negging." This consists of mild, flirtatious negativity, often in the form of giving three-fourths of a compliment. So, if Sam is dressed up to please you, say in white hotpants, a bare-midriff tube-top, and four inch heels, instead of vocalizing the three cheers your genitals are demanding, you say something like "So you're going with that look, huh?"

It may sound cruel, but it is actually what she wants – to be kept on her toes, still striving, never fully arriving. After she screws up her face in a pout, you can of course smile and say something like "There, there, you look OK. Better than OK, in fact. Now get over here and get to work."

Truly unqualified compliments should be reserved for moments when your prick is within her body, somewhere. This is for conditioning, both mental and physical. She's on top, cowgirl: "That was an excellent set of Kegels. Now give me twenty more reps." Or, perhaps she is dutifully slurping away, worshipping your schlong with her mouth and throat: "You're getting really good at this, Sam— I see a bright future for you in cocksucking."

It is also beneficial to continually remind her of exactly how much she is under your sexual thrall. Remember, she enjoys the sex, but she is more motivated by emotional drives, such as her need to please you. It helps to remind her that she has done, continues to do, and will always do whatever you want her to. So, for example, if you hear her running down another girl from school, you can say something like "Sam, you sure seem awful judgmental for someone who is going to take it in all three holes from her foster-father again this weekend." Or on another occasion you can say something like "I think you want me to fuck you in the ass, don't you? Ha! Your asshole just twitched when I said that, didn't it?" She'll fail to suppress her embarrassed smile, because of course it will be true, and she's always amazed that you seem to know those things.

But in general, sometimes the oldies are still the goodies. Perhaps my favorite bon mot is the one I'd use if I were losing a silly argument to her, or if she had just asked for shopping money, or if I needed to relieve some replacement-ref-induced anxiety late in the fourth quarter: "Hey, this cock ain't gonna suck itself, ya know!"

--SD

Dear Stepdaddy: Portentous Panties

Dear Stepdaddy:

I'm dating a passionate woman who isn't shy about making noise when she comes. Nothing too unusual there, but I've noticed a surprising tendency. When her sixteen-year-old daughter is home during one of our "sessions," and can plainly hear us in their small apartment, my girlfriend gets much louder – and nastier. She's always a moaner and a grunter, but having her daughter within earshot brings out the "fuck me you bastard" style of banter as well.

I don't know if she gets off on playing the slut for her daughter to hear, or if it is some kind of competitive mother-daughter one-upsmanship. It wouldn't be a slut competition per se, because the daughter is a gorgeous, bookwormish type who doesn't seem to know how sexy she is and who is most likely still a virgin. I can tell you that whatever the motive, fucking the mother and thereby broadcasting auditory porn for that hot little teen is totally smoking from my perspective.

The longer this has gone on, the more obsessed I have become with the daughter. I think about her while I'm fucking her mom. I'll leave the bedroom door cracked open, to ensure our sound carries further, and in the goofy hope that maybe she'll peek in on us (been reading too many online stories, I guess). And then there are her things.

Yes, her things. I have a key to their place, and often am there by myself (whether leaving in the morning after they've already gone to work and school, coming by to fix something, or arriving early for an evening's visit). This has come to include a great deal of time poking around the youngster's room, her closet, and her things. Most commonly, her underthings.

They are a delight. Most are demure white cotton, both her panties and her bras (she's a tidy B-cup, I've so discovered). I lay them out on the bed. I touch myself. I even go through her hamper, and am occasionally rewarded with a freshly worn pair to sniff. Let's face it, I'm becoming sickly fixated on the daughter's sexuality, and having access to her panties is just about the opposite of a cure.

So that's my situation, and here is my question: What should I do? Should I get the hell away from this relationship before I do something stupid with the daughter? Should I stick to fucking the mother and enjoy my fantasies as just that – fantasies? Should I make like a character from a Stepdaddy story, and figure out how to fuck the daughter behind her mom's back? Or should I just satisfy those urges by proxy, and constrain myself to "fucking" those adorable white cotton schoolgirl panties?

Perplexed in Plantation

Dear Perp:

You have only two choices – drop that girlfriend immediately, or expect to work inexorably towards an attempt on the daughter's succulent virtue. Since you are writing to me of all people for advice, I can assume you've already decided not to take the first, wiser choice. Your judgment in counselors says a lot about your likely judgment in matters hebephilic.

The reason I say these are your only two choices is because your other choices – fantasizing about her while fucking the mom, and using her dainty underthings as onanistic aids – will eventually lead to you to making a move on the girl anyway, so you might as well admit that and plan (scheme?) accordingly, right out of the gate.

Now bear in mind, although you will certainly make a bold attempt sooner or later, you may not be successful, and that can lead to private embarrassment in front of the daughter, to exposure before the mother and the consequent outrage and recriminations, or even to criminal prosecution. I see you are writing from Florida, which has an absurdly elevated age of consent: eighteen years old. It staggers belief.

Anyway, on the other hand, you may be successful. If you study the Stepdaddy corpus carefully, you have a very good chance of succeeding both in despoiling the teen and in enlisting her in a conspiracy to keep the affair completely hidden from her mother. In that case, the rewards are almost infinite. Sweet teenaged pussy (and mouth, and anus). An athletic, elastic vagina that springs back into shape quickly, no matter how many times you batter it mercilessly. A young charge you can teach to be a sexual creature with no hang-ups, no boundaries, and no limits – an honor for you and a gift to her. And I promise you, that first time it hits your tongue, you'll swear her pussy is the finest thing you have ever tasted.

And on the way to that nirvana, by all means blast your spend all over her briefs. Heads up on one thing, though. I myself am a panty aficionado. See my Laundry Day, my Advent: A Calendar of Cum, and my Driving Heidi Home, among others, as evidence. In fact, haiku seven from my Celebration of American Adolescents pretty much sums it up:

Panties unlaundered
On such altars I offer
Creamy thanksgiving

But take it from me, no matter how fascinating they are at the moment, once you start fucking the daughter your obsession with her unoccupied panties will wane. At that point, you'll be only interested in her holes and wondering how you can get your hands on a pair of her cute best friend's knickers to yank over in your free time.

One last word of warning. Once you have used and abused her delicates drawer, trumpeted an ongoing sexual play-by-play from her mother's bed, found some way to guide the girl into thinking she is seducing you, taken all three of her cherries, and maybe even knocked her up, you'll think you can tell her anything. You can't.

You can tell her how you schemed, and planned her defloration all along. You can tell her how much you prefer, and will always prefer, the younger stuff, and that someday soon she'll be too old for your tastes. You can tell her how much you'd love to fuck each of her girlfriends. You can tell her how you'd like her to learn to eat pussy, especially those of the aforementioned girlfriends. But don't ever tell her about the private panty parties you once enjoyed with her things – you don't want her thinking that you're some kind of a perv!

Dear Stepdaddy: Parental Pandering

Dear Stepdaddy:

You perverted bastard, you are ruining my daughter's life, and turning me into something reprehensible at the same time!

I am a single mother, and my daughter Whitney is fourteen-and-a-half. The economy has been hard on my employment efforts, and as a result I have had to accept temp jobs for little money. Naturally, I have cut out most of my own entertainment and social life to save money, but luckily my apartment building comes with free Wi-Fi, and using a laptop I took as "unofficial severance" from my last full-time job, I can at least lose myself in the web for a few hours, especially once Whitney has gone to bed.

My problem is that I stumbled upon your stories. Now although as young teen (and as an older teen, and as a young woman, and now, as a 34-year-old single mother), I fantasized about being mastered by an authority or father figure, that shit never happens in real life, at least not in mine. Yes, I had a stepfather, and yes, he pervingly leered at me in my teens, but he was gross and thankfully I never fell into his clutches. But like many girls, I masturbated furiously about a fantasy father-figure, usually in my mind some amalgam of the middle school principal, my uncle who was, sadly, deployed far away most of the time in the Marines, and whichever salt-and-pepper haired actor happened to be popular at the time.

Reading your stories has led to my having fantasies of my teen years as I wish they had been. You are a disgusting, horny, and perceptive son of a bitch. Your stories also gave me new insight into the way human relations really work. And the use I made of that insight makes me hate you, hate men in general, and most of all, hate myself. Oh, and it also makes me come like crazy.

I said money was tight. Well, after reading one of your stories, I think it was Stepdaughter: Spanked and Fucked, I was so horny that one jilled orgasm alone couldn't seem to quench the fire it had ignited. As I prepared to take a cold shower, I got a call from the building manager. Naturally, he was after the overdue rent (I know, this sounds like a fuck-story cliché!). The problem was that I was maybe a hundred bucks short. Anyway, I knew the manager, Mr. Andrews (yes, he's never shared his first name – I think it gives him a power trip over the tenants), was always checking me out. But as I said, I had just been reading Stepdaddy, so I was both horny and attuned to your disgusting hebephilic wavelength. As a direct result, I did something that sent me – and eventually Whitney – down a horrible path. I went to the manager's office to barter my ass for a rent discount. But worse, I went only after first squeezing into Whitney's school uniform.

Yes, I saved my hundred bucks, that time. And again the next month. But the uniform, role-playing aspect gave Mr. Andrews – and my suborned pussy – some inappropriate ideas. He and I came to an agreement. I could save $500 the next month, and $200 each month thereafter, if the uniform was filled by its rightwise occupant – Whitney.

I'll spare myself the shame of recounting the despicable details. Any reader of your stories can easily imagine the methods of manipulation and subtle deceit I used to get Whitney to eventually welcome Mr. Andrews to her bed. What also happened, a bonus that is often missing from your stories, was the mother's – this mother's – experience: hiding in Whitney's closet, masturbating outrageously, while watching this fifty-year-old man take my daughter's virginity. She was by this point mostly biddable to his demands, but when she resisted at the final moment, and Mr. Andrews had to use some physical restraint in order to successfully split her open for her very first time, did I run out and put a stop to it? No, damn you Stepdaddy, instead, feeling like I was watching a real-life Stepdaddy story unveil before my eyes, I came.

As you probably expect, after that first initial reluctance, Whitney soon came to enjoy servicing Mr. Andrews, even though he is nothing to look at. The bastard tries to get a little extra between the rent payments, but I always insist he make an additional contribution of some sort. That and, of course, I always make sure to watch from the closet and abuse my clit to the scene, although the man (or men, as you shall see) doesn't know about that part.

It turns out, however, that the job market hasn't really gotten any better for me. In fact some of the temp jobs are at the most inconvenient times. For example, when the computer repairman came back to get paid, I had to skip that day's offered temp bullshit in order to arrange for and then clandestinely enjoy Whitney's "discounting" effort. And now, between the cable guy, the local beat cop, the mailman, and several regular visitors all named John, I no longer have the time (nor much of the need) to accept the temp jobs anyway.

But you are an asshole, Stepdaddy! My daughter's innocence is ruined, and my cunt is a sore and sorry piece of work, stuffed and stretched as it constantly is by dildos of all shapes and sizes, and clit-diddled raw with every "session." And I have like zero employment ambitions anymore. Sure, we're now meeting (or bartering) all of our expenses and socking away a couple thousand more a month, tax-free, but the two-way mirror I had installed in Whitney's closet door, the hidden video equipment I want, and the sex toys and batteries I use aren't cheap.

Stepdaddy, I blame you for my situation and for Whitney's. How do you propose we make this square?

-- Projecting in Portland

Dear Pro:

I see what you mean. Compensation is clearly due. I'll be around on the evening of the fifth of next month. I don't expect nor want any of the money I've inspired you to earn, but I will gladly take a royalty payment in kind from Whitney's youthful vagina. Lay in some extra batteries for yourself, I have a lot to teach her.