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.




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.

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