"500 Stories": A Look Back

April

One of my biggest surprises was the number of men who liked dressing up as a woman, or who at least fantasized about doing so. That led to my first discovery of sissy stories, sissy videos, and the shocking popularity of hypno-sissy videos (which I didn't understand at first, since they're made so the male watching them imagines himself being all the girls in the video). That was the inspiration for a new series (one I really need to finish one day) called Hypno-Sissy: Becoming a Cocksucker, which won best fetish story of the month. I'll talk more later about the explosion of popularity in sissy stories and requests for them.

May

One of two stories from the epic Cheerleader's Mom series was recognized as a best of the month. This win was pretty self-explanatory from the title, as the mom gives in completely to her dominant daughter in Cheerleader's Mom: Fucking Her Ass.

June

The first of four chapters in my favourite Rebecca series to win the monthly prize, in the series switching back and forth from the present day to the 1950s, in 1950s: Housewives' Pet Training. I'll discuss my Rebecca collaborations later, but here's a teaser from this lengthy lesbian series.

July

The final chapter of my marathon Cheerleader's Mom series is perhaps its best (rare in a series, as was each chapter having a higher score than the previous), as the mom dines on a variety of delicious pussies in Cheerleader's Mom: Mom's Lap-a-Thon.

Here are a couple of delicious scenes where the submissive mom is allowed to discover the thrill of being in charge:

But then her daughter arrives for a threesome:

August

Another Rebecca collaboration, in MILF's Teen Crazed Cunt Fantasy for best illustrated.

September

Rebecca again (both the artist and the principal story character borrowing her name), with the seduction of her best friend in 1950s: Lick and Fuck Best Friends, where the entire seduction plot is based on this fun book.

November

An illustrated story with my own artwork this time, where I created many of my own fantasies before fulfilling one of them, in Jasmine's Secret: Caught and Seduced.

A couple of the best fantasies in this one include:

A threesome:

A BBC:

A cheerleader:

But it's a shy nerd who discovers my secret and turns me into her pet.

December

A very different illustrated story, and the only one I've done with Wilt, was based on only a few of his drawings and a twisted as can be plot, where a minister misuses his power to fuck his parishioners, and eventually his own daughter on her eighteenth birthday, in Daughter's Initiation into Kink (the second chapter in a twisted trilogy). The story was as twisted as can be, challenging religion in many ways (by the way, I do believe in God, I just don't always have much faith in churches... yes, pun intended).

Here are some of the outrageous pics from part 1 of this delicious tale, Daughter's Initiation into Incest:

As you can see, these pictures are all very edgy, and although I received a lot of great comments and requests to continue, I was also issued a couple of messages informing me I'm going to burn in hell. (Which hasn't yet happened... so far, so good.) Things went even more taboo in the second part and the monthly winner, which I illustrated myself when Walt disappeared, Daughter's Initiation into Kink. That said, here's the lone wild pic he did create for the sequel:

By the way, although I didn't win, I was nominated for most influential author of 2016.

2017

1. I had four best illustrated stories in 2017, before Literotica took a good 15 months or so off from awarding monthly contest stories, and although they did continue running the story contests, they also didn't do any year-end awards in 2017 and 2018. The four stories were three sequels: Sister Surprise: A Kinky Day (January):

Daughter's Initiation to Lust (April)

1950s: Munching the Cheerleaders (May):

I also did a new romantic story for Valentine's Day, where a wife finds many fun ways to surprise her husband, in A Happy Marriage: A Stockings Tale. It included kinky surprises like: eating ass at his office, and giving him a cum-coated foot job...

A foot job, and cum all over her soles:

The story was also a how-to guide to spice up your marriage, boasting a variety of sections like 'Tips to make your man act like he is 20 again. Part 1: Things you should already be doing!' (Page 2 of the story)

This list included:

1. Dress classy on the outside, but like a skank underneath

2. Spice it Up: Sex in Public

3. Watch Porn Together

4. Read Erotica Together

5. Masturbate Together

6. Try a new position each time

7. Do a strip tease for him

8. Naughty Texts

9. Roleplay

10. Toys

So... she roleplayed being Batgirl.

Then there was 'Tips to make your man act like he is 20 again. Part 2: Tasks for the Adventurous' (Page 4 of the story). Which were:

1. Fun with Food

2. Blindfold Him

3. Bondage

4. Watch Kinky Porn

5. Make a Home Video

6. Spanking

7. Fisting

8. Anal

9. Threesomes

10. Pegging

It also included a fun top 17 kinky positions all couples should try, including this one (go to page 4 of the story to see all 17 of them). I won't list them all here, but they're worth checking out, and here's the one I thought was the hottest:

15. Mission Possible

This is our favourite unique position, and one that will fuck you deeper than you possibly imagined, and at angles you didn't know existed (this is, for many, the ultimate g-spot position). Of course with such amazing benefits, it is very difficult to execute. As a woman, you almost become a human pretzel and not only have to literally bend over backwards, you have to be able to hold that position while he slams into you (thus the need for both your hands to support your back). He can also use both of his hands on your ass to keep you in position. Often a woman can't hold this position for long, or even get into it at all, but if you're up for this one, you'll likely have the orgasm of your life.

That led to the wife making her own sexual bucket list SOMETHING EVERYONE SHOULD DO... SO GO MAKE ONE... RIGHT NOW... YES, I'M YELLING AT YOU!

1. Get gangbanged.

2. Have a lesbian encounter.

3. Fuck a black man.

4. Walk around in public with a Full Load of Cum on your face

5. Make a porn film

6. Be completely dominated by a stranger

7. Take it in the Ass

8. Public Sex

9. Threesome

10. Go to a swingers' party

11. Pegging

12. Be fucked Air Tight

13. Go to a Nude Beach

14. Go to a Glory Hole and Open your Mouth

15. Obtain a full service massage with the happy ending

16. Fuck Channing Tatum

17. Make a naughty audio

18. Have half a dozen orgasms in a single day

19. Do a sexy photo shoot... maybe a 1950s set

20. Get fisted

LADIES: HOW MANY OF THESE DO YOU HAVE ON YOUR LIST... AND HOW MANY OF THEM HAVE YOU FULFILLED?

How many of these did the Happy Couple fulfill... go check this one out if you haven't already, or go re-read it, as here I've only shown a few of the hundred-plus pics.

2019

January:

Monthly contests returned with the last part of A Sister Surprise: Drunk Mom, which would also go on to win best illustrated of 2019.

March

Another Rebecca story: Twisted: Blackmailed into Incest, although it is scored my lowest Rebecca story by far (it must have been a slow illustrated month).

June

My first essay win. A short different one, called Sissy/Cock Sucker Dictionary.

November

The most recent of the 1950s series, 1950s: Naughty Bride-to-Be.

December

Two stories earned recognition:

Hedonism Island: A BBC Discovery the first in a series that's both a great collaboration (with Interqueen), and my first actual comic.

A second essay of the month was my third annual Q&A essay, this one called Twenty-Two Questions,which also won essay of the year.

2020

February

Both wife and husband explore their same sex curiosity together, in the hot group sex story that was awarded best fetish story of the month, in Spiced-Up Marriage: A Big Surprise.

Here is a fun picture of the couple after submitting sexually to each of their same sex fun; they're now enjoying the recipient couple returning the favour.

March

My favourite model story yet, was a fun new story about my personal fantasies, where the amazingly hot NYLONKITTY once again allowed me the use of her photos, in Jasmine Fantasies: Nylon Seduction.

July

My first celebrity recognition came in the sequel to Modern Fuck-ily: A Sisterly Lust, called Modern Fuck-ily: Daughter Pets,both of them anally focused lesbian stories.

November

After a bit of a slump, although I'm still surprised Daddy Daughter Date Days didn't win when it was released (a rare incest story that did really well score wise on its release), I earned my second celebrity recognition with Willow's Way Ch 2, where Willow sodomizes Faith on multiple occasions (obtaining a surprising 4.82 score). And I earned another illustrated best of the month, with a lengthy tale about myself (mainly), called Christmas Carolyn: A Lesbian Orgy, my editor Tex's first attempt at illustrating. Here's one from that series, depicting a moment in an after-prom party:

December

Just announced as the final edit was being made for this essay, I earned two more best in its category awards. One for my fourth and definitely longest and most ambitious essay Twenty-Two More Questions which is the most in-depth look at the thing I like as well as analysing all my favourite stories I have ever written with commentary (the list, without the commentary is at the end of this essay and is a great read in my humble opinion).

The most recent from the Best of Both Worlds: DP'd by BBC also was recognized as the best... a series that is just beginning to role. Here is pic of me in a double penetration position I can't fathom I could pull off in real life but looks fucking fun.

10B. CONTEST WINS

I have now won many contests... and I think I've also come close many times. I'm still surprised Hedonism Island didn't win. That said, my first win wasn't even one I consider among the best of my stories, although it was the first one about me, Taking Jasmine Walker in the 2012 Summer Contest, where while on holiday, I'm seduced by a younger woman. My editor considered illustrating the scene where she fingers me at a table in a pub, or when we have sex in a hotel elevator, but in the end,q he did this sexy balcony scene (which unbeknownst to him [Until now Jasmine, and that's Way Cool], is exactly what I did during my honeymoon in Jamaica).

Stocking Tales: Becoming Boss's Pet was my second win. An illustrated story originally, the pics were deleted at the model's request. That said, here are a couple that don't hint at her identity:

Lez Awakening: Halloween Hijinks was a 2018 Halloween Contest win, where a curious girl confirms to herself and others she's a submissive lesbian at two consecutive invitation-only private parties.

My editor loves this story, and decided to create two pics for it. Here's his explanation for the two:

The first one is Mistress Janice Adams fucking our protagonist (Lola's very first time), while Lola licks the amazingly beautiful Lexus to orgasm.

But we didn't get to see Lola's beautiful face (or her scandalous nurse costume). Too bad about the costume, but I seized upon the very last paragraph of the story, so we could get to see her face (and also Lexus's from the front).From left to right, we see Mistress Janice, Lexus and Lola. (Remember: Mistress Janice made a point of requiring her two lovebird subs to wear identical outfits, as they all attend the November occasion together)

10C. YEAR-END AWARDS

I've been nominated for three years so far: 2015, 2016 and 2019 (there were no year-ends awarded in 2017 or 2018).

2015

Incest story of the year: What Mom Knows Fucks Her Mom

Illustrated story of the year:"Moms & Daughters": A Family Affair

Anal story of the year: Kinky Tales: I Pegged my Husband

Fetish story of the year: Kinky Tales: Jock Gets Pegged

2016

Illustrated story of the year: A Shemale Submission: A Lust Story

Transgendered Character of the year: Annabelle from A Shemale Submission: A Lust Story

Illustrated story of the year nominee: Stocking Tales: Becoming Boss's Pet

Nominated for most influential author of the year.

2019

Illustrated story of the year: A Sister Surprise: Drunk Mom

Essay of the year: Twenty-Two Questions

Transgendered Character of the year: Kimberly in BBC Shemale: A Beginning

11. REAL PICTURE STORIES

I've only done a few pictures with real models, as they are very hard to come by.

The first was an amazing collaboration with Vanessa in "Stocking Tales": Office Submission. Here are a few of the pics she created especially for this story.