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Digital Desires #2

Conquered by Clippy: An Erotic Short Story

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Christie Aackerlund doesn’t need help with anything. So when the world’s biggest technology company offers to fly her to a remote location and investigate an alien artifact, all by herself, she’s all like “I’ll do it!”

But the artifact isn’t what it seems, and soon an overly helpful giant living paperclip is getting her all bent out of shape.

Conquered by Clippy is a 4000 word short story featuring sexual situations with digital assistants. It’s for super mature audiences only.

68 pages, Kindle Edition

First published March 10, 2015

105 people are currently reading
435 people want to read

About the author

Leonard Delaney

20 books46 followers
Fully ignoring the lame advice to "write what you know," Leonard Delaney uses a vivid imagination to overcome limited life experience. His unique blend of erotica, fantasy, and science fiction explores the lighter side of massacring good taste. His debut novella, Sex Boat, is two parts parody, one part satire, with a sprinkle of sea monsters.

See http://www.forestcitypulp.com for more information about Leonard, or email him at ldelaney@forestcitypulp.com

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5 stars
80 (14%)
4 stars
42 (7%)
3 stars
78 (13%)
2 stars
142 (25%)
1 star
224 (39%)
Displaying 1 - 30 of 233 reviews
Profile Image for Peter Topside.
Author 6 books1,466 followers
May 3, 2025
I’ve fantasized about a lot of different office supplies over the years. Staplers, colored pencils, 3-hole punchers, and who could forget that alluring laminator machine. Is it just me or is it hot in here? But I remember when I first opened Microsoft Office and saw Clippy pop up back in the day. He just had that look. That look that made me think ‘That paperclip is a slob. A true sexual deviant.’ And now look, I was right. So there wasn’t much here, but we follow the same character, Christie, who is banging her way across all sorts of inanimate objects, trying to help mankind somehow. She is now on a dangerous journey helping some random guy locate more alien technology. I thought she was a journalist, but here we are. Anyway, she ends up shagging Clippy. He rocked her like a hurricane and then it just ended. My brain hurts reading this stuff.
Profile Image for Manda.
58 reviews2 followers
August 20, 2022
I’m only admitting to reading this because I’m behind on my reading goal.

Profile Image for Marc *Dark Reader with a Thousand Young! Iä!*.
1,518 reviews320 followers
June 29, 2024
Update: because life is like that, I just now read a passage about Clippy in an unrelated book, within days of reading this story:
Do you remember Clippy? That’s the cartoon paper clip in Microsoft Word from the late 1990s. You would open a new document and start writing and it would just up and force its fucking self into your attention and say “it looks like you’re writing a letter!” and try to offer all these unhelpful writing tips while you look around for the X button to shut it down. I think they also called it Office Assistant, if that rings a bell. If you don’t know what I’m taking about, try to imagine a cartoon character who just walks up and takes a shit on your face while you’re trying to work.

Thankfully that exact scenario does NOT play out in this story. I now return you to my original review.

********************

What is a free Kindle Unlimited trial for, if not to sample some weird erotica? My only regret (well, maybe not my only one) is its effect on my Amazon book recommendation feed. It barely recovered from my last KU free trial, and now it will start all over again.

Hey, remember Clippy? Ever wondered what it would be like to be fucked by a paperclip? Then this book is for you.

Naturally, Kissing the Coronavirus is the gold standard for this type of material. But this Clippy story came out five years earlier, so maybe it's not a fair comparison. Would I have found this story as boring if I had never read that other? Probably still yes. The framing story is not very interesting, and the sex scene, when it finally gets to it, is unexciting. There was a good basic idea in the main character, a fiercely independent woman who chafes at the idea of getting assistance from anyone, for anything. Otherwise, a few tame Microsoft-related jokes are the only potential draw.

But, BUT . . . I appreciate this Kindle title because—surprise!— it included the story I actually wanted to read (but didn't want to pay $0.99 for): Humping the Hambandit. I'll review that one under its own book page.

This kindle book also includes Pounded by Pluto: The Crappiest Planet but I didn't care to read that one.
Profile Image for Kelly.
239 reviews20 followers
July 15, 2022
A masterpiece of women's erotica. No one can compare to the raw sexual energy of Clippy.
Profile Image for Maggie.
29 reviews
Read
August 7, 2024
I feel like the author popped four beers, cracked their knuckles, and hammered this out in one session without any help from Microsoft Word’s spelling & grammatical functions. Unfortunately, it just wasn’t funny enough for me, although the title is magnificent.

(Apparently I do have standards.)
Profile Image for Grapie Deltaco.
853 reviews2,656 followers
September 15, 2022
“Lady-butter”

That’s all I have to say about it.

(Also the story ends at 22% and the bonus story for this one is about the Hamburglar)

CW: explicit sexual content, sexual harassment, death
Profile Image for Clutch My Pearls Podcast.
144 reviews116 followers
May 7, 2024
We're a podcast for smut!
*We rate every book 5 stars, we're here for the smut*

No icks allowed. 5 stars.
It looks like this story is haunting you, would you like some assistance with that? (vagina).

Episode 30, "Conquered by Clippy"
Profile Image for Cassandra.
1,343 reviews101 followers
July 26, 2022
THE GIRL WAS TOO STUNNED TO SPEAK?!?!?! LMAOOAOASJDNASKDA

I-

Truly, and I mean this from the bottom of my heart, HUHHHH?!?! How does one COME UP WITH THIS LMAO?

Leonard. Leo. Nardman.... what is actually going on here. This was something else. I... I don't know what to SAY?

I have to go into hiding.
Profile Image for Diana.
10 reviews5 followers
July 17, 2015
Even more ridiculous than the first book in this series. Best summed up by this line: "Yes, Clippy! Assist me! Assist me hard!"
Profile Image for  Bon.
1,349 reviews202 followers
February 5, 2023
While I suspect this was not at all written in good faith, like an anti-Chuck Tingle, it was hilarious.
Profile Image for Kelly (AndKellyReads).
1,009 reviews60 followers
Read
April 15, 2023
Reading this was a group effort and I think all of us ended this story with more questions than with which we began.

Also this book is an incredible example about why sex ed is important in schools.
Profile Image for Alex | | findingmontauk1.
1,571 reviews91 followers
November 5, 2022
I think I officially lost it when Clippy said he was "Microhard" as a play on Microsoft. And I am not even sure what "lady-butter" is but it scares me.
Profile Image for Biblio.
Author 8 books229 followers
Read
May 2, 2025
Just as dumb as the first one but funnier. But also cringier. Clippy is a legend though so auto 5 stars. Miss that little silver fucker. I’m not here for plot but what happened to the Tetris baby? I need to know.
Profile Image for Gemma.
143 reviews682 followers
July 22, 2021
LAS RISAS SEÑORES😂😂😂 menuda maravilla
Profile Image for Natasha.
366 reviews5 followers
January 3, 2026
listen... I had a lapse in judgement. I promise I'm not the type of person who reads these.


however, this was a wonderfully passionate and erotic tale of two lovers. 10/10
Profile Image for Stephanie.
27 reviews9 followers
April 26, 2023
If I ever needed to write a paper on why men shouldn’t write erotica, I would use this as my main argument.
Profile Image for Jon.
883 reviews15 followers
March 14, 2015
Hysterical and horrible, but man, the voice of Clippy is spot on *perfect*
Profile Image for Alicia Ceasar.
1,737 reviews19 followers
February 7, 2023
Format- Kindle Unlimited

L I S T E N this is what drives me crazy about these books. Look at the title, look at the cover, read the blurb. If you are going into this thinking it will be some revolutionary addition to the literary classics of the world, turn yourself right around because this is not the book for you. It’s not even trying to market itself towards you.

This is a book for when you want to grab a glass of wine and giggle your way through 25 ish pages of silliness that is full of tongue in cheek humor and nods to pop culture. I hate seeing people give books like this 1 and 2 stars. Bffr what did you expect when you started it? Because when I downloaded this book, this is exactly what I expected.

The KU version actually has three short stories in it and they are all immensely entertaining if you just want something silly that will make you laugh. I read several of the lines in this collection to my partner and we both laughed until our stomachs hurt and if that isn’t a sign of a good book, I don’t know what is.
Profile Image for Gia Davis.
342 reviews163 followers
June 5, 2023
What the actual f*k

This is all you get
- She felt his warmth push past her pussy, toward her internal organs … including her heart.

Goodbye
This entire review has been hidden because of spoilers.
4 reviews
August 23, 2024
Amazing really reccomend! If you want to laugh tho, if youre looking for a serious book dont read this.
Displaying 1 - 30 of 233 reviews

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