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Dear Stepdaddy: Training Tools

August 30, 2013
Posted at 1:26 pm

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 its 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.

I'm stretched so much before I reach that point that I'm afraid to push down further. Sometimes I think a should just lift my legs at that point and let my weight slam me all the way down, put I always lose my nerve before I can try it. That idea usually seems best when I'm doing something else, like laying on my back playing the butterfly against my little button. When I'm straddling the tub edge with almost a coke can of toy cock up my hole and six more inches to go, it seems a lot less possible.

Anyway, Stepdaddy, you may be wondering why, with all those other sex toys to play with, I even want to try to take that monster balls-deep. Well, this part might gross you out the most of everything. You see, I can't stop thinking about that dildo, ever since the first -- and then the second -- time I saw my own dad's prick!

That's right. The first time was about two weeks ago. Dad was staying with us for a few days, and I walked in on him in mom's bathroom (actually, their bathroom when he's here) because I like to use their jacuzzi tub. Dad was just out of the shower, dripping wet, and was rubbing a towel through his hair and over his face. That's why he didn't see me at first, and why my eyes locked onto the fat cock hanging between his legs! It was huge, just hanging there, thick and long, with really big balls hanging from a sac behind like a chandelier (not like the dildo, which has its balls up snug against the cock base). Obviously, I didn't get down and measure it, but I certainly couldn't have covered that hanging cock completely if I grabbed it with both hands -- and I'm not sure my fingers would have reached all the way around it, either. And that was while it was soft!

The really embarrassing thing was that when my dad moved the towel away from his head and eyes, he saw me in front of him staring right at his penis! Thank God he was cool about it, and didn't freak. In fact, he didn't even try to cover up, but just stood there and smiled, like he didn't mind that his own fifteen-year old daughter was like salivating over his Daddy Cock. I broke the spell after a second or two and turned and ran back to my room, locking the door in embarrassment.

Notice I said salivating over his Daddy Cock. I could say I was staring at his penis in shock, or disgust. In fact, that is exactly what I did say, to myself. At first, that is. But only for a few seconds, because lying on my bed, my pillow over my face in shame, I felt my fingers slide under my pajama waistband, past my little patch of pubic hair, and onto my pulsing clit. The pussy below it was gushing, and it didn't take me long to come. After that, it didn't take me long to pull out the particular toy I had stolen from Mom's collection the previous night, which happened to be the seven inch cock-shaped dildo. That slid in easily and it wasn't long before I came again. But when I pulled that toy out, slick with my teen-aged juices, I realized that it wasn't near as big as my dad's cock had looked -- soft!

This is so embarrassing, like I warned you, but that afternoon I set up the laptop Mom keeps in her room, putting it on her dresser with the screen off but the camera on. Sure enough, it captured video of my dad fucking my mom. Of course, it wasn't always focussed in on his cock, and they weren't always in the right position, but the video captured enough to prove that when hard, my dad's cock was at least as big as that ten-inch dildo. No wonder my mom owns that one!

Anyway, I don't know why, bit ever since that day I am like totally obsessed with my dad's giant cock, and I've been trying to get that huge dildo all the way in my hole. But Dad is gone again, back chasing his teenaged bimbos, so I can only work on the dildo when I have Mom out of the house for a guaranteed period of time -- which hasn't happened often enough in the past two weeks for me to make much progress -- nor to keep my pussy happy with the attempts.

So Stepdaddy, how can I, a fifteen-year old girl, get myself a dildo of my own, and not just any dildo, but a huge, penis-shaped dildo, with balls at the base, and a suction cup, and that has a shaft at least ten inches long, as long and as big around as my Dad? It's not like I can just walk into that kind of store, and even if I did and they didn't kick me out, I'd be way too embarrassed to go up to the counter with a monster cock like I need. What should I do?


Dear Snugfit,

I think you will be able, with my advice, not only to acquire the educational implement you desire, but at the same time make another of your wishes come true.

But first, let me commend you. I think you are a very brave girl, despite your protestations of the meekness and shyness which have kept you, to date, from entering seedy adult book stores in your school skirt and ponytail. The reason I believe you to be bolder than your words suggest is that I have very much enjoyed the photos you sent with your email. You are very cute, and your bare little breasts make my dick quite hard. You demonstrated your courage in sharing them with me.

But I especially enjoyed the other photos you shared: those documenting of your dildo efforts. The ones with the seven-inch realistic penis are impressive, and I loved the sequence of watching its progress, from its kissing at the mouth of your adolescent vulva (with your downy, light brown tuft of wispy fur) through its full, balls-deep intrusion. Good girl!

But my word! To then see the photo-montage of your developing pelvis attempting to skewer itself on that giant, ten-inch dong was breathtaking! Your description of it is definitely accurate -- that is one fat fucker. If the image of your underaged ninth-grade cuntlet stretching itself around that mammoth rod weren't so fucking hot, it would be downright adorable in its precociousness!

But I fear that a little photographic analysis on my part, using the several photos you provided covering presentation, positioning, mounting, descending, and engulfing (to your current depth-limit), has led me to determine that your estimation of being able to already accept four inches of that gigantic bastard are a tad optimistic. I would say that, although you do seem able to "swallow" the full knob of its silicon glans and a bit more of its absurdly unfair girth into your drooling, overtaxed girlbox, it appears that so far, you can only take three inches of its length. I know, you can go much deeper with the smaller dildo, but that one doesn't make nearly the volumetric demands of the tool with which you are obsessed. Never fear, this simply means you have that much more joyous work ahead of you than you thought. Seven more inches and even greater girth.

So, lets get to it: my advice. I do not think you need to go to stroll into an adult book shop in order to complete your quest. You simply need to enlist some aid -- and the agent I have in mind is someone who is already predisposed to appreciate the hungers of teenaged girls (albeit girls a bit older than you, heretofore -- at least as far as we know), and someone who seems to take some pleasure in contact with your nubile form, and lastly someone you would like to attract to your presence with more frequency. In short, I think the best approach would be to confront your dad during his next stay, maybe even as he comes out of the shower, wielding your mother's monstrous fucktoy, declaring "Dad, I need you to buy me one just like this." This approach will have the likely side benefit of demonstrating to you that his erect prick is indeed as large as the toy, since I suspect it will immediately swell to its full turgidity when he sees that big fake cock in your small hands.

I predict, based upon your father's described character and lack of self-control, the hebephilic delight your photos reveal you to be, and the compelling eroticism of handling that dildo in front of him like a starved cockhound, that this approach will lead to three successful outcomes, two of which you didn't even know you were asking me to help you with.

1. Your father will obtain for you an oversized dildo of your very own, just as you wish.

2. Your father will spend much less time away from home, and very likely will move back in for good.

3. Your efforts to train your schoolgirl vagina to accept the oversized dildo will soon be fast-tracked by the repeated introduction into that slick orifice of an erect, fleshy appendage that is almost exactly the same size.