Sir, Please Don’t Put That In My Bum
Go and check out Lilu’s site for more information on the TMI Thursday tradition. Essentially, you write a post in which you give too much information. You do this on Thursday. See how that works?
Let me explain something to you. You know how yesterday I posted that really embarrassing vlog? This story is so much worse. So.Much.Worse. The upside? Its not about me! Score!
Background information: I went to the nerdiest and most awkward college in the history of education. It was like 99.87% male, and the guys were awesome and sweet and smart, but also? Most of them? Not super experienced with the ladies.
Okay, so its 2002 and I am friendly with a certain fraternity member, we’ll call him Jack (because that’s his name because that is an awesome alias). I’m 20 billion percent sure that Jack had never seen a real live naked lady. This much was very obvious. Evidence? He called breasts “boobies” like in a totally serious, trying to be sexy way. Like, “Oh man, I’d love to touch her boobies!” Did you just throw up a little? I know. But man up, because its only going to get worse. Jack has clearly never had sex, but he talks about “all the chicks he banged back home” basically non-stop. Apparently, Jack thinks his right hand is several chicks. Sad.
Around this time I also had a very trampy friend named Heidi (total alias or is it). Jack thought Heidi was very doable (by the by, men? doable is not a compliment. just wanted to pass that info on.) and he told her so at a particularly drunken party. Heidi was suitably impressed and now felt like removing her panties. And it was on. Magical? I thought so too.
Cut to Jack’s room at the frat. Heidi’s naked, Jack is naked, intercourse is imminent. Jack refers to Heidi’s breasts as boobies. Heidi is a little concerned, but figures he was just trying to be funny. Or something. Foreplay continues. It gets a little oral. Then Jack bites Heidi’s vagina. Let me repeat for you, he.bit.her.vagina. Not like super hard or anything, but apparently it wasn’t pleasant. So Heidi is all, “Um, what are you doing?” And he’s like, “Oh, my old girlfriend used to like that.” Red flag number two. Which Heidi ignored. And the hooking up continued. Heidi is such a trooper!
Fast forward to an indeterminate time later. Intercourse commenced. Heidi suggests switching positions. She tells him she would like to do it doggie-style. Jack seems hesitant. He’s like, “Oh, I don’t know…” But Heidi isn’t taking no for an answer. So, she gets on all fours and then… he inserts his penis in her ass. Because that’s what he thinks doggie-style is. Heidi is not happy. Things end poorly. She is yelling at him. He is insisting that, “that’s what doggie-style is!!” Then Heidi left and told everyone that Jack was a virgin who didn’t know the difference between anal and doggie-style.
And that, my friends, is way more awkward than a tranny hooker vlog.
I swear to you, doggie style IS anal.
Signed,
Guy totally not named Jack
I don’t know which is better—this story or that picture. Jack is pantless! Heidi is topless! (But she has the decency to cover up her bits with a nice little skirt. Oh, how tasteful, Heidi.)
I absolutely love this blog, saw in on It’s Unweavable, and had to check it out. You are too hilarious!! I keep going back to read past posts, because I can’t stop laughing
[...] Jill Pilgrim’s Sir, Please Don’t Put That In My Bum [...]
Every once in a while, in the heat of the moment, the P may connect with the A. But not knowing the difference? Lame.
I’d be pissed as hell! And completely humiliated if I was Jack. Great story, thanks for sharing!
What the hell, Jack? What kind of guy doesn’t like doggy style?
And, seriously, he just rammed that thing in there? No warning? Nothing? I hope Heidi also pointed out what an infantile pecker he had.
i love that it was worth it to her to mock Jack’s lack of bedroom skills while totally giving away exactly what they did. cost/benefit analysis: cost of embarassment to heidi for sleeping with a virgin and letting him do that apparently was less than the benefit of making fun of jack with everyone!
Unintentional anal will ALWAYS be awkward.
OUCH. I like my anal to be announced and planned.
moooog- the jig is up, I know your true identity now.
Hannah- Heidi is pretty classy with her covered lady bits.
S.Elisabeth- thank you so much!!!! You’re my new best friend
Just- yes, exactly. Accident, forgivable. Ingnorance, unforgiveable.
Taylor- yeah, Jack was not even close to humiliated enough by the incident.
MJenks- Seriously! Come on, guy!
Lusty- yeah, math wasn’t really Heidi’s thing.
Sarah- words to live by.
Maxie- First of all, give me jeans. Secondly, agreed.
You went to college with Heidi Montag Pratt??! Awesome!
Anal sneak attacks are NEVER okay.
Hahahahahahahahahahaha::gasp::hahahahahahahaha!
I agree with justjp and sarah on the sometimes it’s accidental (to which I’ve always announced, “Whoah! Wrong place!” before it gets too far), and that the unintentionalness of such an accident is always bound to be some sort of awkward.
But for Jack to actually try to convince Heidi that that’s the way doggy style is supposed to “go”??? That guy is a tool. I feel sorta sad for him, and certainly hope he grew out of his toolness. GAH!
“It gets a little oral. ”
Maxie, someday when you are at my wedding telling the “how we met” story, please to work that sentence into the toast.
Now THAT’S awkward.
I’m still stuck on the fact that he bit her vadge… I definitely would’ve kicked him in the face.
Ohnononono…Jack, just no.
Jill, you’ve reminded me of YET another story – about my sister, her first time with her new bf, and a lip ring ‘incident’.
I’m totally going to update my blog today.
Oh man, poor Heidi.
OK, I gotta say it. What a jack ass.
You know, I’m not a student oof doggy anatomy, but as far as I remember from having all my female dogs fixed, they still have girly bits! And to top it off, biting her? Love nibbles are OK, but seriously, you don’t bite hard! I’ll go with KrisAKAJaney on this one, what a JACK ass.
Hahaha! You have the best/most awkward college stories. It seems that, at the party, Heidi was wearing a lovely skirt and Jack was completely naked. I’d say it just went downhill from there.
LOL Oh my lord, that’s horrifying. Totally, completely horrifying.
Shannon- oh my God- that would have made the story so much better!
Faith- I somehow doubt he grew out of it. Call it a hunch.
LiLu- Yes, Maxie definitely needs to work that in, please vlog that.
Julie- Um, yeah. Not.Okay.
Terri- I think I’ve heard this story, but the Internet hasn’t so get on it!
Courtney- Amen, sister.
KrisAKAJaney- You made me laugh. Out loud.
Bret- yeah, he was clearly unfamiliar with both sex and dogs.
Brooke- Dude, its because I went to the most awkward college ever.
Kyla- Yes, horrifying really is the word for it, huh?
Does Jack also think dogs shit puppies out? Because really that’s the only way that would make any sense.
And I’m pretty sure Heidi gets a brick in her bungalow in heaven for not immediately murdering him…just saying.
So yeah… I happen upon your blog yesterday, thanks to your “Tranny Hooker” vlog on Miss Liz Marie’s It’s Unbeweavable… and all I’ve been doing is snickering and snorting in my office-cave at the hilarious shiz-nit you write about. OMG, you are effing hilarious!!! Good thing they’ve shoved me in the basement, Office Space style, so they don’t discover the source of my snickering… prolly wouldn’t go over so well with the bosses
That’s just disastrous for all parties involved, but I think the real victim here is the act of sex itself. What a shame…
Heidi is such a trooper!!!
What kind of porn was he watching? Biting vag’s and doggy style=anal….pour soul.
Also,
I love you.
I’m wondering how long she let him “carry on” before stopping him.
Had the boy never watched porn? Read a dirty magazine? BEEN ON THE INTERNET?
Oh. My. God.
Am now wincing and giggling at the same time. Vagina biting? So very, very ouch.
PS. I think the whole doggie vs. anal thing was just a not-so-clever excuse.
Haaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa! Poor Heidi, whoever she is.
P.S. Your anti-spam bot actually made me use my brain to do math skills. WIN.
WTF? Who bites vag? That is messed up. Period. And for him to try to say his ex liked it is messed up. Unless maybe she was into the kinky pain stuff but being that Jack is such a boober I doubt that.
Dani- Hahaha, oh man, I wish I had thought of that line before I wrote this story!
Jessi- Thank you so much!!! I am so happy I am able to entertain you in your cave! <3
timoteo- truer words. Sex really is the victim here.
LIZ! I love you. That is all.
Lexa- He clearly was not paying close enough attention. And Heidi suffered the consequences.
Hope- good point! Maybe Jack is more clever than I’m giving him credit for…
Casey- Yeah, we’re all mathy here. And poor Heidi indeed.
Kellie- Agreed, I’ve never met a chick who’s into vagina pain.
great. now my vagina hurts. how do you even bite a vagina? that, jack, is talent. it’s gonna be “the new move” soon, the vagina bite, they’ll call it. it’s all the rage. with the kids.
eeeeeeeeeeeeeeeeeee (this is me being excited) (you know why)
crossing my legs and laughing hysterically. biting? oh dear.
Hahahaha! I was never into the bitten vagina either. lol
omg. I have to say, you might be my new favorite blogger…omg. You are just too funny. I hope you never find out a horrific story about me and then use my {alias} real name to tell it on your blog! AMAZING!
Okay, first the most amazing vlog ever and now this? I knew my sister was right about you.
BECKEEEEEEEEE- We are going to blow their minds.
emrlds- Yeah, I think leg crossing is the appropriate reaction.
Cass- Dude, TOTALLY!
TheBeautyFile- LOVE YOU!!! Thanks!!!
Gabby- Hahah, thank you! And is there anything your sister isn’t right about?
omg what is wrong with people. with boys specifically haha.
the bad part is you know he totally went out to his friends about the ‘awesome sex’ he just had
I can’t get over the biting. What manual did he read about that in?
Omgggg he just put that in the ass? Hell nooooo. Its hard for me to say yes to that In the first place but if a guy just do it without announcement, ill kick his head.
Ps. She shud had already thrown him out when he bit her in the first place.
Ouch ouch! Heidi must have been traumatized…Er, no Jack was traumatized. Awesome TMI!
Perfect read for Friday afternoon! Jack is a super dork!
“Apparently, Jack thinks his right hand is several chicks. Sad.”
*snort*
Poor Jack.
Poor Heidi.
Poor Jill for having to know all of that crap. How horrifying, darling.
AND WE ARE SO ON FOR DRINKS ON THE EAST COAST. YES.
I literally covered my vag when i read the part where Jack bit her. Oww. Awesome TMI!!
Hilarious but a bit of a worry at the same time – I’m with Erika above with the biting part!!! Ooooh! No we don’t do that were I come from young man!
OMG I am dying over your illustrations…well that and this story….and the tag “that is not my vagina” lol
Wow, he totally misunderstood the concept of eating out… He probably thought “eating at the Y” meant that the YMCA was having a buffet…
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