tagIllustratedAwakening: 7 Slutty Blackmail Tasks

Awakening: 7 Slutty Blackmail Tasks


Summary: MILF's sexual awakening by being forced to do 7 slutty tasks.

Note 1: This is an April Fool's Day 2018 Contest Story so please vote.

Note 2: Thanks to DARKBREEZLY for collaborating with me and creating all the illustrations that bring this story to life.

Note 3: Thanks to: Tex Beethoven, thor_p, Robert, and Wayne for editing.

Note 4: A warning: the 'n' word is used a few times in this story; however it's never used to put anyone down, but only for the glory of worship.

An Awakening: 7 Slutty Blackmail Tasks

Being a teacher means being a pillar of the community twenty-four-seven, 365 days a year.

You are judged at school against the strictures of a Puritanical moral code, but that same moral code must also be adhered to in all public settings.

This joyless approach to public life usually isn't a big deal since I live a rather boring life.

I mean, I haven't had sex in three years, at least not with a real person. Thankfully, with the advancement of sex toys (my rabbit vibe and my personal massager being very effective) I didn't really need to endure the complications of an intimate relationship in public or in private.

My husband left me for his younger secretary just over three years ago (he wasn't a teacher or a minister so he could do whatever he wished without becoming unemployed) and I kept myself busy with teaching, writing a novel that I was now close to finishing, and my kids.

I have twin 18-year-old children, a boy and a girl, who are rather polar opposites and definitely not identical in any possible way.

Donald is very academic with a dozen scholarships to choose between from all the best Ivy League schools, although he hasn't chosen yet. He is a bit nerdy looking, awkward and socially inept, but a sweetheart with a heart of gold.

Charlotte only cares about gold... and her phone... and boys. She is a cheerleader, very outgoing and popular and gets tons of attention from the boys with her red hair, green eyes and large lively breasts. Every month when she gets her period I give a huge sigh of relief, truth be told.

In spite of the strictures on my public life I often spend my evenings watching porn (my favorite video is one of Britney Amber as a teacher masturbating in her class and getting caught and being used by four students... the idea of just being taken, used, dp'd is something so exhilarating and so polar opposite of the prim and proper persona I wear in the classroom) and reading Literotica to get myself off... as I find an orgasm (or two) helps me fall asleep faster. I was thus engaged one Saturday evening in the spring when my life came crashing down in a heartbeat.

My phone buzzed and I saw a text from an unknown number. Since students occasionally text me questions, although today was not only Saturday but also the beginning of a week-long spring break, I stopped rubbing myself, my orgasm just beginning to build as Britney on the screen had a cock in all three holes... something I had never done, never even had two cocks at once... and checked the message.

I gasped.

It was a picture of me sucking my ex-husband's cock!

Shortly after someone's wedding like six years ago.

The accompanying message said: Ms. Ambrose, I never knew this side of you existed.

I couldn't believe it! How could someone have this picture? I remember Barry convincing me to suck his cock in a secluded office adjoining a wedding hall. He often made me suck him in risky places as he got off on it and knew I would do it just because he asked. I am by nature rather sexually submissive and like to be told what to do when behind closed doors... or sometimes even in public, usually when I am tipsy and even more easily persuaded to be naughty. I had sucked my husband's cock in the back of a taxi, in a tent we were sharing with another couple while they were asleep, in an airplane on a trip to London (not in the bathroom where it would be relatively safe, but just under one of those tiny blankets in coach), and in the kitchen when my parents were visiting and watching TV in the adjacent living room. The craziest time was in my hospital bed just hours after giving birth to the twins. He even came on my face that time and made me keep it on my face, although he generously let me rub his cum all over my face so it wasn't so obvious. He had also fucked me at a funeral, inside a phone booth (no matter what Superman may think, those windows don't conceal much), at a beach with others in view and at an amusement park. He'd even had me give him a hand job, and a few quick sly sucks, at our wedding reception while we were being fêted at the head table with over 200 people in attendance. The crazy thing was I always said no at first, but still ended up giving in and obeying him and always got turned on doing it.

Now I want to stress I'm not a slut. Since college I have only ever had sex with my ex. I have to admit that I did go rather crazy in my freshman year of college and fucked maybe twenty guys that year, half of them one wild night at a frat party (all right, I really was a little slut for a while), but then I knuckled down and concentrated on my studies except for a brief lesbian encounter where I licked a girl while drunk at a party. I liked that, but was petrified to be outed as a lesbian and thus never considered doing it again. Once I fell under Barry's thrall I was constantly terrified of getting caught when he wanted to have sex in risky places, but those always ended up being the most pleasurable sexual encounters. The fear factor added such an edge that I just came and came! (And Barry had to stuff my panties in my mouth to stifle my boisterous excitement.) So once I was married I wasn't a slut except when ordered to be one by my husband. That doesn't count, does it?

Then during the past three years after he left I got into reading erotica and watching lesbian porn. I had a few go-to scenes when I was in a lesbian mood including: the always hot Kendra James seducing her daughter-in-law played by Veronica Vain in Almost Caught, the seduction of a son's girlfriend when he was there with Nina Elle and Cleo Vixen called Tasting Cleo, or my all-time favourite where MILF Lolo Punzel seduces her best friend's daughter played by Dylan Daniels while chatting with the mother. I realize in retrospect the idea of getting caught was also a major turn-on in the porn I watched.

As I pondered my slut-hood, or hopefully lack of it, a second text arrived.

I nervously clicked on it and found myself gasping at another picture of myself, this time with a full load on my face.

I recalled Barry making me rub it all over my face like a facial cream before returning to the wedding reception where a friend commented on how shiny my face was. I was mortified, yet that night back in the hotel room I let Barry fuck me hard to multiple orgasms.

This pic was followed by the words: Although I do like your choice of facial cream.

Who the fuck was doing this? My ex? He was the only one who had these pictures, which he'd promised he had deleted the next morning when I was sober.

I called him (he still lived nearby, wanting to spend time with our children, which I parsimoniously allowed) and asked, "You deleted those pictures from the wedding, right?"

"Of course," he answered, after a brief hesitation.

'You're one hundred percent sure?" I asked, and since I was staring at one of them I knew he was lying.

"Okay, okay," he admitted. "I transferred them to my laptop before you made me delete them."

"When?" I asked.

"After you passed out that night," he replied.

"And where is that laptop?" I asked, already thinking the worst.

"Oh God!" he said.


"It was stolen a couple of weeks ago," he said.

"What?" I repeated, even though I'd heard him.

"The house was broken into and a few things were taken," he explained, "including my old laptop."

"And the pictures were still on it?" I asked, even though it was obvious they were.

"Shit, maybe," he said, before adding, "I hadn't used that laptop in a couple of years."

"Fuck, you idiot!" I snarled, and hung up.

I looked at the pictures again.

They didn't implicate him at all... sure his cock was in view and I could recognize it, but that was it.


Another text.

No picture this time, but just as scary.

Ms. Ambrose I'm going to help you re-live that inner slut.

I stared at the words.

Relive? Did this person know me?

I finally responded back: Who are you?

The response back replied: Your one-week Puppet Master.

What on earth did that mean?

I responded: ?

His response realised my biggest fear: If you want these pictures to stay secret and not go to the school board and online you will perform seven tasks I will assign to you.

Oh my God!

I pleaded a response: Please, do you want money?

He responded: I don't want money. I'm doing this for your benefit.

I scoffed.

I responded: For me?

He responded: Yes and that will become clear as the week progresses. Check your phone tomorrow morning. Task one will be sent sometime before noon.

I responded: And if I say no?

He responded: Well, we already know what Superintendent Walsh thinks of breaking the moral code. Any claims you made about not posing for these pictures or the cock in question belonging to your husband would fall on deaf ears. Correct?

My eyes went wide. Superintendent Walsh had let three teachers go for minor things: online twitter comments that were borderline sexist, a teacher who had a nude scene in a movie from ten years earlier (it was actually a real studio movie) and a sexting conversation that an ex-boyfriend released online to humiliate the third teacher.


How did the blackmailer even know this?

I asked: How do you even know this?

He responded: I did my research. Good night.

I responded back: Please, let's work something out.

Unfortunately he ignored three more pleading texts and when I phoned the number it went to dead air.




Not surprisingly, I didn't sleep much that night... petrified by whatever he (I assumed it was a he) had planned for me.


I was stressed all morning, so much so both my son and daughter asked if something was up, yet I just told them I hadn't slept well last night.

I sure couldn't tell them I was being blackmailed by some stranger over sex pictures I took with their dumbass father years ago while we were drunk.

I went to church, like I do every Sunday, although for the first time I checked my phone during the service. Each time my phone buzzed, a nervous chill coursed through me. Four times I received texts, four times they were from friends and not from him.

Each time I sighed a big sigh of relief.

It was five minutes to twelve, the service was over and I was chatting with a couple of ladies. One of them was Fahara, the minister's wife, who was unfortunately somewhat of a bitch, and tended to be judgemental of other people's shortcomings. I was just beginning to think maybe this was all a bad joke when the text came. Recognizing the number, I went to my car to read it.

He texted: Ready for task 1?

I responded honestly: No!

He responded: The question was rhetorical. You are to buy a dildo or take one from your collection (if you have one, I sense you do) and take selfies of yourself with it in your pussy in two public places.

My eyes went wide. He couldn't be serious.

I responded: Please, don't make me do this.

He responded: I am doing this for you.

I already hated this person, but his pretentious he was doing it for me crap pissed me off even more.

I responded, fuming: Don't play the Good Samaritan bullshit. This isn't for me.

He responded: You'll see it is, all in good time. Send me the pics after each task is completed. And have fun.

I responded: And if I don't?

He responded: Your school board finds out and some MILF website gets an exclusive collection of photos starring mine truly. I didn't send you all of them.

I responded: This is blackmail.

He responded: Yes, it is. Now stop delaying and do as you're told.

I snapped: Fuck you!

He responded: Perhaps in time. But at least for now this is about you, not me.

His cryptic responses were so frustrating.

I didn't respond, because it seemed futile.

Instead, I cried.

Ironically, many of my fantasies have included being blackmailed into having sex. In my fantasies it was a turn-on just to let go and be forced into doing things no one would contemplate me doing. I have a few favorite videos about blackmail, such as Phoenix Marie being a journalist who is outed at home as being a pretentious bitch, who ends up taking it up the ass (something I had often been curious about, but never tried) and is used like a cheap slut. I also enjoyed 'Blackmail Our Asses', where two college girls get caught snooping in the Dean's office and end up giving up their assholes (Jillian Janson and Lyra Law both make taking it in the ass look exhilarating). Lastly, as twisted and taboo as it was, incest blackmail was also hot... which I always felt guilty about after I came, but 'Blackmailed Anal Creampie' where a mother is blackmailed by her son always got me wet. I mean I didn't really fantasize about my own children, but the taboo of someone else's incest often got me off.

When I read Literotica I read mostly: gangbang stories, incest stories, the odd lesbian story and in a perfect world when I was lucky enough to find one, a blackmail, incest gangbang story.

I was learning quickly that fantasy and reality were indeed not the same thing. I wiped my tears away and decided it would be easiest to go to an adult shop and pick up a dildo since I didn't have one. I had vibrators and my magic wand, but no dildo, plus I didn't want to go home and have to lie to my kids about why I was coming home just to be going back out.

I went to an adult shop on the other side of the city, where there was virtually no chance to bump into someone I knew. I spent a good half hour at the shop buying not only a pink dildo, but since I was there I ended up also buying a suction cock vibrator that I could use to fuck myself (I really missed bouncing back on a cock, preferably a real one) in my bedroom or in the shower.

I purchased the two toys and then decided to get the first public place shot done right here, right now. It would be relatively safe as I would use a dressing room which had a curtain so I could be heard, but likely not seen. The shop was also relatively empty, which eased my insecurities.

I grabbed some lingerie and asked, while acting dumb, "Shoot, I forgot I needed lingerie too."

The pretty cashier smiled, as if knowing I was going back there to fuck myself, as she nodded, "Use room 3."

"Okay, thanks." I nodded, feeling naughty as I went to the room to obey some stranger who was blackmailing me.

I walked into the room, closed the curtain and began to pull down my pantyhose and panties to my ankles to allow the photo to be taken.

As I was doing this, I got another text. I considered ignoring it, but I hoped maybe he was going to surprise me by saying that this was all just some sick joke.

Instead, he ordered: For all pictures today you may not wear panties or bra.

I sighed, but replied, with one word that I hoped he would understand meant I was pissed: FINE!

I took off my bra, pulled off my pantyhose and my panties, before putting my pantyhose back on, feeling too naked without them to at least cover my almost total nudity, especially with the dress I'd chosen to wear today being a little shorter than normal.

I then concluded it would be easier to get this done if I didn't have to pull down my pantyhose each time, so I grabbed the crotch and tugged. It didn't tear at first, but after a little extra muscle it ripped smoothly, giving me quick and easy access to my pussy.

I sat on a stool, spread my legs, took the dildo out of its packaging and rubbed it up and down my pussy, which was not lubricated enough to allow anything inside, especially a thick dildo. I had bought a thick dildo thinking it would be fun to use at home and really stretch my pussy, but I hadn't considered the reality I wasn't even remotely horny at the moment.

So I pulled up one of the videos that really got me excited called 'Five to One' starring the nasty but hot Veronica Avluv as a reporter fucking five soccer players after a game and taking all five loads on her face.

I'm not going to lie, few would believe that not only do I love sucking cock, but I also love swallowing cum and I get turned on getting a load all over my face. I love the submissiveness of it; I love the feeling of warm cum rocketing out of a cock and splattering on my face; I love the knowledge that no one would ever see me as a woman who would eagerly suck a cock and swallow the load like a porn star or take a load all over my face. Although I had a lot of unresolved fantasies, bukkake was one of my biggest.

I scrolled the vid to near the end as I rubbed the dildo up and down my pussy lips until I was wet enough and slipped it inside me.

As soon as I did, I began fucking myself slowly before realizing he hadn't said I had to come. Very well, I wasn't going to come for him.

No, fuck him.

So I turned my phone to camera mode and took a selfie that I hoped made it pretty fucking clear how much I didn't enjoy this.

As soon as the shot was taken. I pulled the dildo out of me, and put it back in the bag along with my panties and bra.

I then tried on the lingerie; I figured I should buy something to make it look less obvious I had just fucked myself in a change room. The lingerie fit well, a simple black nightie reserved for the day I finally found a man I wanted to impress. I returned to the till and purchased the nightie even as I could feel her eyes boring into me, her sly smile telling me she knew exactly what I had been doing in there. Plus, as she looked at my blouse she seemed also to notice I was no longer wearing a bra.

She didn't say a word about it, but humiliation burned through me.

Once in my car, I reluctantly sent the picture with the text: Done!

I wasn't sure where I was going to do one more picture as I checked my email. I was responding to a student asking a question about an essay due after break when he responded: That picture didn't seem too public. Photo #2 must have other people in it. Also, don't look so miserable. Fucking yourself is supposed to be pleasurable.

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