Dear Stepdaddy -- the 2013 Annual

by Stepdaddy

Caution: This Humor Sex Story contains strong sexual content, including Ma/ft, Consensual, Humor, Incest, Father, Daughter, Uncle, Niece, Teacher/Student, School, .

Desc: Humor Sex Story: Stepdaddy's amusing and erotic advice column compiled for 2013 -- PLUS all-new, never-posted before material! Five different confused teen girls seek Stepdaddy's wisdom, and unsurprisingly, he rises to each occasion.

Dear Stepdaddy,

I'm in eighth grade and now I got a problem. It was all fine until last summer when Mom married Roy, my new stepdad. No, it ain't what you think, Roy's not fucking me. Though I know my age's not bothering him, since he is screwing my friend Tabby. He doesn't know I know, but her and I tell each other everything.

The problem with Roy is that he makes me get good grades. Mom never cared much, but Bob says if I don't get good grades, he's gonna make me go to summer school this year! Really, he probably don't care about my grades, he just wants me out of the house all summer so he can fuck Tabby while Mom's at work and I'm at school. Roy is a fireman so he has weird shifts and all, so that'll leave him lots of days when that little whore can worship the bastard's cock every which way. She's so stupid, she thinks she's in love with him. Don't get me wrong, Tabby's my BFF and all.

Stepdaddy, my problem is that Mr. Renfrew, my social studies teacher, is fucking me like every day after school. I mean, that's not exactly the problem, since I came on to him, though not 'cause I'm into him (he's not that bad though), but because I'm getting like a 'D' in his class. That first time I tried to be sly about it, to get him to make an offer of some kind, but he played dumb until I basically stripped and climbed up on his desk. Then he knew what to do, and has like every afternoon since. Mr. Renfrew fucks me pretty good, and he always cums inside me, without protection. That's not my problem, either (although when I asked him if he was scared I might get pregnant, he told me that was my problem, not his). It's not my problem because my stepdad pays for my birth control pills. Not that he knows that ... he thinks he's buying the Pill for Tabby, but she already gets the Pill 'cause her mom is cool. So she gets Roy to buy them, then she gives them to me. That was her idea – she's pretty smart, she gets 'Cs' and 'Bs' like all the time.

No. My problem is that my quarterly report card came out, and Mr. Renfrew gave me another "D"! Maybe it's kinda my fault, since I never really mentioned when I started fucking him that I was doing it for a better grade. Anyway, after the report card, I tried to bring it up to him, but Mr. Renfrew told me to quit whining, then he pushed me down to my knees and pushed his cock into my mouth, saying "I'll show you what that hole is for." Anytime I try to talk around that big thing of his, he just jams it in further. That's how I learned to deep throat.

So now what? How do I get Mr. Renfrew to fix my grade and not have to go to summer school? I know he doesn't think I'm smart enough for better grades, 'cause he always calls me...

Young, Dumb and Full of Cum

Dear Young Fun,

I don't think better grades lie in your future. In fact, I don't think grades are going to figure prominently in the path your life takes, regardless. But I do actually have two valuable pieces of advice for you, young lady.

First, I think you should get yourself an enema kit from the drug store and use it before dropping by Mr. Renfrew's class from now on. The reason I suggest this is that you sound very much like the other side of the tale I heard from another correspondent, someone who sounds very much like your Mr. Renfrew (is that in fact your real name, "Gloating in Galveston"?). He is a an eighth grade social studies teacher who has asked me how to add some spice and variety to his daily debauching of, as he put it, "his ditzy little fucktoy." Based on my advice to him, I strongly suspect that a great deal of "ass-to-mouth" lies ahead for you.

As for your grades, you can forget about that. Whether your teacher is in fact "Gloating in Galveston" or simply another pedagogue blessed with good luck, he is unlikely to broach his professional ethics and alter your grade -– at least not now that he has no incentive to do so. You should count on his cum leaking out of all three of your holes from now until June, and plan on seeing a "D" as your final grade.

However, don't lose heart! Even though you are never going to be a scholar, I think you are a wonderful person. I would go so far as to say that you are, and will continue to be, a true blessing to mankind.

From reading your letter, it is clear to me that your real objective is to avoid summer school, not to get a better grade for its own sake. Happily, I have solid advice for you on that front. At your next opportunity, simply offer yourself up to your stepfather, Roy, in the same manner you originally did to Mr. Renfrew. I'm sure his dick will be inside you in short order.

Now here's the important part, can you try to remember this? Roy is going to be thinking that he will need to keep his playtime with you separated from his playtime with Tabby – thinking he has to keep each of you secret from the other. That means by fucking him, you'll be actually increasing the likelihood that he'll send you to summer school! BUT, if you look him in the eyes that first time, while he's long-stroking your middle school muffin and before he cums, and ask "Roy, do you think you could help me learn to be bisexual with Tabby?" you'll be fine. With that on the table, there is no chance you'd even be allowed to attend summer school.

-SD

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Dear Stepdaddy: Virgin Waxing

Dear Stepdaddy,

There is something so embarrassing about me I don't know what to do. First of all, I look very young for my age. Although I'm fourteen-and-a-half, I look like a twelve-year-old, I swear. It makes me feel so shy sometimes. And I need confidence if I ever want to try out for American Idol – you know, stage presence and all that.

My voice coach is the only person who doesn't treat me like a little kid. He talks to me like an adult. In fact, he keeps treating me like an adult even when his wife isn't there, so it's more than that he's just trying to be inclusive. And unlike most folks, he doesn't act like I'm some kind of delicate, breakable doll – when he needs to put his hand on my lower back to adjust my posture, or place his palm on my abdomen to check my diaphragm work during a breathing exercise, he's not shy. If he thinks I'm not trying hard enough, he'll goose me! He doesn't know this of course, but since it's usually just him and me alone in their studio during my lessons, I get funny feelings – good feelings – when he is touching me (especially "down there."). Stepdaddy, afterwards, at home, I sometimes play with myself thinking about him. I like feeling like an adult.

But here's what's embarrassing. I don't have any pubic hair, I never will, and it's all my own fault.

Oh, I'm physically mature enough – I've been getting my period for two years now. But several years ago, when I was about nine, my mother read an article about "virgin waxing." This is where a girl that age waxes her legs, long before she really needs it. The idea is that once she goes through puberty, she'll never really grow any leg hair and won't have to wax or shave, because the follicles somehow get trained that way by the process.

So my mom showed me how to do it – wax that is – and I can promise you, it works. Even today, two years into puberty, I have no hair on my legs. I mean none, not even tiny blond ones, like I used to have. I also have no hair under my arms, because after I started doing my legs, my mother came up with that idea and said I'd thank her some day for thinking of that, too. But Stepdaddy, I did something foolish. On my own, I decided to wax my pre-pubescent legs a few more times, without my mother's help, and I got a bit carried away. Over time, section by section, I ended up waxing my body entirely from the neck down, including my crotch –- and even my butthole area a few times! I was just a silly girl then and didn't even know anything about sex parts, really – I was just having fun with the waxing, and anywhere I could spot a tiny hair, wooosh! off it had to come!

But now that I'm so much older, it's terribly embarrassing. For example, in the shower room after gym class: here I am, already a very young looking girl (I don't even have A-cup breasts) sporting a completely hairless body, having to shower among a bunch of girls who actually look like fourteen-years-olds, or even older – they have bigger boobs, and pubic areas that grow out into a bush or, if they shave or wax, you can at least still see the shadow or bumpy texture that proves that they are old enough that they can have pubes if they want them.

How am I ever supposed to get self-confidence when I have to endure that humiliating comparison three days a week? This embarrassment isn't going to help me command the stage, now or ever.

Wish I was "Carefree in Colorado"

Dear Hairfree,

You dear, dear little thing. Thank you for sharing your story with me. I am quite familiar with the "virgin wax" concept. I myself have never directed its use, basically because I do not associate with girls when they are eight or nine (why would I bother with them until later?). However, I have encountered a situation not entirely unlike yours before.

One of my investments is in a trailer park – I'm a part-time landlord and I occasionally find myself on-site, chasing down a rent check or to doing some minor repair to the plumbing or electrical hook-up of one of the units.

Three summers back I had the pleasure of dropping by one of these units for the overdue rent, only to find that the single-mother who rented the place was out, and her fifteen-year-old daughter was home alone, naked and as hairless as you describe yourself to be. (And by the same process -- I later learned that her mother, a stripper by trade, had virgin-waxed the girl some six years earlier, at the age of nine. Unlike in your case, her mother had done this as an investment in the girl's future, akin to how some parents invest money in their kids' music lessons or invest their time in some developmental activity like the cub scouts). Having entered the trailer using my own key, I surprised her in the act of languorously petting her bald little kitty as she sat on the couch in front of the TV watching Rikki Lake, or some such show.

I know this may not sound like it has anything to do with you, Hairfree, but take note of how this sweet little thing, barely older then than you are now, reacted to the potential embarrassment of being seen naked and permanently free of body hair by someone who was to her a complete stranger – and a large, male, much older complete stranger at that. Was she mortified? Humiliated? Not at all. She smiled, withdrew her hand from her crotch, spread her knees a bit further apart, and said "would you like to take over?"

Naturally, as my adult readers understand and as you will appreciate yourself someday – hopefully someday soon – when confronted with such a flawlessly smooth pudenda, my first order of business is to take a taste. Let me tell you, the texture of that hairless, stubble-free, never-been-anything-but-smooth little cuntpuff was a delight. Eating her sweet pussy went from being my first order of business to also being my second through seventh orders of business! If she hadn't eventually sobbingly begged me to stop eating her to yet another orgasm and to finally fuck her, I might be between those thighs to this very day!

So, what's the point? Well, that girl, to whom her mother had already thoughtfully given the birth name of "Vixen", is today fulfilling her ambitions. She is stripping five nights a week on various local stages, and has the fan following she always hoped for. Luckily for her career, in all my numerous subsequent visits, I never marked her flawless belly with the stretch marks concomitant to a Stepdaddy breeding (at least not yet, although now that she's eighteen, I have higher-priority, younger tummies to try to swell, so maybe she'll never have the pleasure).

So you see, what you consider an embarrassment – a handicap! – can actually be instrumental to following one's dreams. Vixen chose not to be embarrassed by her hairlessness, nor by the slutty tattoos and body piercings her mother had also so kindly provided her with. Instead, she chose to use her condition to help her reach her full potential.

You can do the same. Instead of worrying about what the other eighth grade girls think about your body, why not find out what your (apparently straight) male voice coach thinks about it? I suspect that if he becomes aware of your permanently unfledged condition, he will redouble his efforts, and spend even more time mentoring his little songbird of a student. He'll feel obsessively compelled to attempt certain "big girl exercises" far earlier than he had previously intended. He'll insist on extra lesson time, at no additional expense to your parents. You might even get some more voice coaching in. I'm certain you'll get plenty of new throat exercises. Not to mention breathing training as your diaphragm accommodates unaccustomed bludgeoning stresses from below.

In order to make all of these good things happen, I suggest you attend your next lesson in a short skirt, going "commando." That means without undies. When he puts his palm on your tummy to check your "deep breathing ability," gently push his wrist down until his hand slips under your skirt hem, saying something like "don't you want to check my "heavy breathing ability?" I promise you, one feel of your smooth, hairless, and probably quite slick little vulva, and you will immediately become your voice coach's number one student.

With that kind of attentive coaching, before long, you'll be lighting up the airwaves on American Idol, with all the body-image confidence and accompanying stage presence you could desire. Or, if that fails, you can always fall back on an alternative show business career. By then, Vixen's following will probably be tiring of her then-twenty-one-year-old offering and eager for someone a little "fresher" to adore.

-SD

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Dear Stepdaddy: Age Inappropriate Behavior

Dear Stepdaddy,

Could you help me get the word out to old dudes like you that teenaged hotties like me don't need or even want you to try to act, talk, or accessorize like our generation?

Take me for example. I like boys around my age, or a little older, to be cute, and "cool", and up with all the latest style, slang, and so on. But why would I want that from a forty year old man? If I'm interested in guys that age – and I am – it's totally because they don't feel the need to try hard to fit in and keep up with the "cool kids." They got it together and are so above worrying about peer pressure and about what's "in." Well, that and because they really know how to fuck a girl good.

Maybe you can share my situation to show some of these dudes what not to do, and what to do.

I'm in ninth grade. In our town, instead of being the lowest grade at the high school, ninth grade is the highest grade in the middle school. So this year, me and my friends are the big deal on campus if you know what I mean.

Anyway, an example of an older guy trying to be cool to us teenagers is Barry, the band teacher. I mean really, it starts right there – of course we call him Mr. Germaine in front of other teachers and our parents, but he always encourages us Bandies (that's the kids really into band, who hang out in the band room sometimes after school or during the lunch hour) to call him by his first name. He's always texting me, and trying to have conversations with me and others like the ones us kids have with each other. He dresses way younger than his real age (which is somewhere in his thirties), has piercings, and so on. Like just today, during my one-on-one clarinet lesson, in one of the little practice rooms back behind the main band room, he was like showing me where he wants to put his next tattoo on his arm and was asking me my opinion of which design he should get. I know, right? What is impressive about a grown man asking the opinion about something like that from a fourteen-year-old girl?

I found it so dweeby of him that I almost didn't let him finger me. Almost.

Now, let me give you a different example, so you can see how it should be done. Mr. Grogan is one of the ninth grade math teachers. I know his first name is Robert, but I have no idea if he goes by Robert, Rob, Bob, or what, because every student knows better, without his ever even having to say so, that there's no way we can call him anything but Mr. Grogan. He doesn't have piercings, he doesn't have any tattoos, he doesn't know the first thing about the latest music or memes, and he certainly doesn't send me or any other student texts.

Instead, he simply fixes his eye on me during class, gives me a slight nod, and my pussy starts slobbering. That's because that little nod of his tells me that the other two math teachers won't be around in the math department office after school – Mr. Jacobs because, like most other days, he'll be coaching football, and Mrs. MacArthur because, probably, that it's a Friday and she and her husband like to take off immediately for their lake house.

And the reason this information makes me so wet is that it means that about thirty minutes after the final bell, when all the other kids are long gone, I'll be lying on my back on the sofa in the math department faculty office, getting my pussy long-stroked by Mr. Grogan's very grown up cock.

Mr. Grogan doesn't ask my opinion about tattoos, pop music, or his personal fashion choices. Heck, he doesn't even ask me if I want it in my mouth, my cunt, or my asshole. He makes all those decisions and that's that.

So that's the message I hope you'll spread, Stepdaddy. We teenie-twats do want teenaged boys to fawn over us, try to guess what will make us like them, and just all around submit to our manipulation. It's fun, and let's face it, sooner or later we'll probably marry someone in our age group.

But when it comes to the MEN in our lives, we don't want a friend, or a cool buddy, or a hip peer. Basically we want men to be in charge and to teach us, not try to be one of us.

Eager Pupil

Dear Eager Pubis,

Thank you for your letter. I know exactly what you mean. I've observed so many would-be hebephiles getting this wrong.

I for one leave youthful fads to their rightful generation. Perhaps I sound like a fogey, but in my day, at least our styles weren't permanently disfiguring, like excessive tattoos or earlobe stretching. My Members Only jacket was as goofy as any fad ever has been, but at least it has been in the dustbin of history for a couple of decades, and I'm no longer stuck with it. But some of these body mods? Please.

It is funny, this behavior you dislike. Why do the men who attempt to be "teen cool" think that those girls interested in older men would be attracted to this? Do they imagine that these biddable babies admire the teen boys sniffing around them so much that they want access to more of the same, albeit of grayer hair and perhaps stouter build? Absurd.

Now my dear, I am certain you understand that the opposite also obtains. Connoisseurs such as myself certainly do not want you pretty little things trying to act like any generation older than your own, either. If girls your age want to sport belly button rings, or to shave your baby cunts totally clean, or to follow the lead of trampy celebrities and wear short skirts with no undies, I say "be yourself" – that is, be true to your adolescent need to do whatever is currently considered by your peers to be the cool thing to do.

I should admit that I have recently made one exception to these rules in my own life. I come from a generation of men who do not customarily shave themselves below the neck. In short, we are not metrosexuals. Nevertheless, when my fifteen year old stepdaughter proved to me that she could finally properly tea bag both of my testicles together, and indefinitely, without gagging or suffocating, I conceded to her request and began to shave my scrotum. Apparently she finds it difficult to ball wash my entire sac for the lengthy sessions I require when a stray pubic hair detaches and finds its way into a maddening, tickling enlodgement at the back of her throat. But you will note, this isn't a concession to a cultural fad on my part, but rather a thoughtful consideration for a properly dutiful young girl.

-SD

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Dear Stepdaddy: Training Tools

Dear Stepdaddy,

I have to start by saying everything I am about to tell you makes me feel very awkward. And although, since discovering your stories and columns I have often found myself masturbating to descriptions of situations like mine, I am still hesitant to confess, even to you, and even anonymously, my story.

I am now fifteen. About a year ago I discovered in my Mom's closet a locked security box, with a keypad combination. Now, at the time I was delighted to guess right that the combination was my own birth date, you know, like this : d-d-m-m-y-y. Over time, now that I have snuck into that secret stash like a hundred times, it has started to sort of freak me out that my mom would use her own daughter's birthdate as the combination to her collection of sex toys! That's right, I said collection, because in that box there are: three penis-shaped dildos of different sizes and colors, two that have balls and suction cup thingies at the bottom, and one of those two is ten inches long (I've measured, that's from the tip to where the balls start); two "regular" butt-plugs, one sort of slender and one really fat (I didn't know what they were until I did some research on the internet), plus one butt-plug that vibrates, and then several vibrating toys that I've figured out work on the pussy in different ways: one is sort of a tube with a roundy-pointy end; one is kind of bent over at the tip, which feels really good against the front wall of my insides, about four inches in (I told you this was awkward!); and one that looks like a butterfly and feels real nice when I hold it against the outside of my pussy, especially against my clitty thing near the front.

I don't think it's surprising so much that my mom has these -- after all, looking back, there was always a present or two to her from Dad every Christmas that she'd open and then giggle, and not let me see what it was, so she probably got them all from him.

And it doesn't surprise me that nowadays, she needs to use them a bunch, 'cause Dad is hardly ever around. Mom says he's having his mid-life crisis (he's forty-four), and so he's moved out to an apartment in the city where Mom says he's busy chasing the "young stuff." She's not happy about that, of course, but she says he'll get it out of his system and come home for good. I hope so, 'cause I miss him most of the time.

He does come stay at home on some weekends, holidays, sometimes for like a week, but he always leaves again, according to mom it's when he gets the "itch".

I don't want to give you the idea that he has abandoned me. He sends me texts all the time and we talk on the cell-phone he got me. And when he visits he spends lots of time with me and pays me tons of attention, with hugs, and gifts, and spankings. What I mean is, he likes to swat me on the behind, but it's not like when I was little, and he did it when I was bad and he was cross or something. Now he gives a quick spank when he's in a good mood, like after we've been playing in the pool. And I used to be afraid of getting a spanking, but now I like it (weird, huh?). Stepdaddy, sometimes after all the hugs and stuff, when Dad swats my butt I get a serious urge to break into Mom's special box as soon as possible! Actually, when he's around is when it is safest to steal one of her toys for a little while, 'cause she doesn't use them when she has him here.

But always, he only stays a few days at most and then it's back to his 18 and 19 year old girlfriends in the city (I've been all over his Facebook page and he's not shy in his photos section, so I've seen what some of his "girls" look like, and they are YOUNG!) Anyway, I wish he didn't need to chase teenagers so he could be home with Mom and me all the time. Mom says he'll grow out of it, but I don't want to wait!

Anyway, that's not why I am writing to you. I am writing to you because of my own gross urges. Like I said, when my dad is here to take care of Mom, it is easy for me to "borrow" one of her toys. But when he is gone, I can only get at them when she is at work or busy, and then I have to return them and lock the box before she gets back, 'cause otherwise she might find one missing (she could feel her own "need" at any time when Dad's not here).

The thing is, Stepdaddy, I need my own toy, but I'm only fifteen, so how am I going to get one? And this part is really embarrassing, I need one toy in particular – one just like my mom's biggest penis-shaped dildo, with the balls attached and with a suction cup. Let me back up a bit. I started out using Mom's smallest penis-dildo. I worked up to the middle-sized one, which has like seven inches of "shaft" and it has a suction cup, which I figured out how to attach, upright, and the side of the tub, which I can straddle and slide myself up and down on like I was really fucking a guy.

In addition, I think I kinda already mentioned that I like the bent one (it says "G-Pleaser" on the side if that helps) and the clit-tickling butterfly. Now, here I'm getting gross again, but I've also used the slender butt-plug (which is really nice with a vibrating toy in my pussy at the same time) and the vibrating butt-plug, too. The only thing I haven't tried is the big fat butt-plug. I might try it, but I'm afraid it might permanently stretch my butthole out too big!

I can say I've tried everything else besides that giant butt-plug, but that doesn't mean I've "taken" everything else. The really big dildo – the one with ten inches for the cock part plus balls the size of tangerines – that one I haven't taken fully. I've mounted it on the tub-edge with its suction cup, and I've lined my little pussy up with the tip and pressed down. It's hard at first just to the get the big head in (although it feels nice once I have!) and then as I try to slide down the shaft, I can only go about four inches or so (which is weird in one way, since I can take all seven inches of the other one). The thing is, that dildo is thick! It widens as it goes down, and is thickest at about six inches from the tip, where I swear it is as fat as a Coke can.

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Story tagged with:
Ma/ft / Consensual / Humor / Incest / Father / Daughter / Uncle / Niece / Teacher/Student / School /