Awakening: 7 Slutty Blackmail Tasks

I licked her while she was on her back for a couple of minutes before she said, "Come and finger fuck me," as she changed positons and was suddenly on all fours with her lovely ass arched before me.

"You say the sweetest things," I teased as I moved behind her and slid two fingers inside her pussy.

"Oh yeah," she moaned, "finger bang me."

That was not a term I'd heard before, but I obliged, plunging my fingers in her as deep as they could go and as fast as I could.

She squirmed as she stretched out her legs, allowing her cunt to spread open wider.

As I fingered her, I wanted to lick her, but my current position didn't allow that.

So I pulled my fingers out, quickly flipped myself onto my back and slithered under her before sliding my fingers back in and reaching up to lick her.

"Oh," she moaned, but although I could lick her in this position, I couldn't finger bang her as hard or as deep and after a couple of minutes she decided, "Time for a little face sitting."

"I thought you'd never ask," I joked, as I quickly got onto my back and watched as she moved into position and lowered her glistening pussy onto my face, my tongue extended before it was even within reach.

I eagerly licked as she said, "I fucking love this position."

"Me too," I concurred, between licks.

And for a good few minutes, five, maybe seven or eight (I certainly wasn't keeping track), I licked and licked.

This position was amazing as besides being completely at the whim of the woman above you, her sweet scent was enveloping me. It was like hot box heaven.

I could have lain in this position for an eternity but she suddenly rolled off me and sighed, "Sorry, leg cramp."

I laughed, as she collapsed backwards, "At least it's not me."

"It's definitely not you," she smiled, as she stretched both her legs high in the air.

A sudden wicked idea popped into my head once she was done with her stretching. I lifted her ass up, pulled her entire body up against mine and dove into her cunt.

"Oh my," she moaned, as I devoured her cunt.

I licked, I sucked on her clit, and I tongue fucked her.

Her moans increased and as she was getting close she moved her hand to her clit and began tapping on it.

My aggressive tongue and her fast-paced slaps on her clit, something I would have to try on myself one day soon, had her moaning like crazy and seconds later she screamed, "Fuck!" as her orgasm hit her and her cum squirted out of her and onto my face... squirting being something I'd thought only happened in porn movies.

My face was coated with cum as I opened my mouth to catch as much as I could as if it were ropes of cum.

She kept slapping herself, her body vibrating against mine, as her orgasm flooded out of her.

When she was finally done, she said, "I've really got to pee."

I joked, "How can you have any liquid left?"

"I'm an enigma," she shrugged, getting off the bed.

"That you are," I agreed, before adding, "first door on your left."

"Okay," she hurried out, "be right back."

I got off the bed and went downstairs to get a drink of water. I downed a glass and then poured two glasses of wine before returning to her.

When I returned, she was on my bed, still naked, and said, "I hope you don't think we're done yet?"

"God, no," I said, hoping this night would last forever. "Just figured we could refuel and maybe put some more liquid in our bodies."

"You did drain me," she said, with a wicked smile.

"I do love cum baths," I shrugged.

"Me too," she said, as she accepted the wine.

I sat on the bed and we silently sipped our wine. She asked, "So where are your children?"

"Across town at their father's," I answered.

"Does he get custody every weekend?"

"Twice a month," I said, before adding, "and every second holiday."

"That sucks," she said.

"It's not ideal," I agreed, "but I got primary custody and I'm happy they'd both rather be here than with him."

"If you don't mind my asking, how did it end?" she asked.

"He cheated on me with a younger woman," I revealed, somehow feeling comfortable telling her the truth.

"I'm sorry," she said.

I shrugged, "I'm long past the sad stage. Although I still haven't gotten past the bitter and angry stage."

"Well, I think his loss is other people's gain," she said, finishing her wine.

I agreed, "Truth is, I don't want to be with someone who doesn't want to be with me. It's just that the kids were caught in the middle."

"At least now they're adults," she said.

"And in a few months I'll be all alone," I said, the idea of empty nest syndrome being my biggest worry the last while... well, before the whole blackmail thing.

"Maybe you won't be alone," she smiled. After a quick kiss, she asked, "I'm assuming you've never been to Le Chateau Club?"

"I don't even know what that is," I replied.

"A female version of the Fenway Club, but for anyone," she said, before adding, "anyone female that is."

"A lesbian club?" I asked.

"Yeah, and it can get pretty wild," she said.

"Wow," I said, the idea of going to a lesbian club pretty intriguing.

"You can dance, you can eat women under the table, get fucked onstage, ride a Sybian, or taste the most amazing pussy in the world," she said.

"Isn't that yours?" I smiled.

"Mine is damn good," she agreed. "But Big Rosie's honey is legendary."

"Big Rosie?" I questioned, my eyes going wide. What were the odds there was more than one woman in Boston named Big Rosie?

"Yeah, she's a black woman who women will line up to dine on," she revealed.

"That sounds crazy," I said.

"I thought so too until I lined up, for almost an hour, before tasting her amazing cunt," she said. "You've got to try it one day."

I pondered telling her I had already tasted big Rosie, yet I wasn't sure I was comfortable telling her about the blackmail. I mean, I thought about it. The idea of having someone to talk to about it was appealing, yet somehow I felt like I needed to finish this path myself. I felt sure as we became closer I would eventually tell her. I said, "Well, I guess you'll have to take me there one day."

"That can definitely be arranged," she agreed, leaning in and kissing me.

We kissed for several long minutes.

As we kissed, I thought about Big Rosie and the crazy coincidence that the one woman I'd met on Craigslist would turn out to have a legendary pussy. But she had tasted amazing; there couldn't be any mistake this was her.

She then asked, breaking the sweet intimacy and honest conversation, as she moved her lips to my ear and warned me, "I'm going to fuck your ass later tonight, baby."

"Words I did not imagine ever being said to me," I trembled. The idea of being ass fucked was a turn-on in theory, but so far a disaster in reality.

"Don't you want to give me your ass, sexy?" she asked, tugging at my earlobe.

"I want to give you my everything," I admitted, just her soft, nasty words, her hot breath and her lips enough to make me a submissive mess in seconds. I added, "But I've tried it before and it didn't go at all well."

"You haven't had the right partner," she pointed out.

"That I haven't," I agreed.

"Anal sex is about complete trust, especially the first time," she said, as she nibbled my earlobe, kissed my cheek, then my lips, then my other cheek, before replicating the attention on my other earlobe.

"Okay," I agreed again.

"Do you trust me?" she asked, as she shoved her tongue into my ear.

The question was so full of possibilities! In truth I barely knew this woman. Yet sometimes you just know, and I did. I nodded, as I admitted, "Yes; don't ask me why, but I do."

"Unconditionally?" she asked as she moved away from my ear and looked me in the eyes.

Maybe it was my submissive nature, maybe it was the look in her eyes or maybe it was just my nature to trust, but again I admitted, "I do." And after a pause added, "Unconditionally."

"Good," she smiled. "Because I want to be the one to take you there."

"Do you want to be my Mistress?" I asked. Could I have a Mistress who could be both intimate and caring, but who also understood when to be in control? In most stories I read or videos I watched the relationship was pretty much dominant versus sub at all times. And in truth, there were times where I did just want to be used, or fucked, or dominated, like I'd been with Ms. Martinez or at the glory hole... yet other times I wanted tenderness and intimacy. Could I have my pussy pie and eat it too?

She smiled, "Do you want me to be your Mistress?"

"Yes," I whispered, nervous at her response.

"I expect complete obedience," she warned.

"You'll get it," I committed, meaning it.

"But whenever I decide, such as for the next few moments, I'll just be your sweet girlfriend. Let's take this journey together, shall we?" she said, smiling wide.

"Oh my god! That combination is a dream come true!" I said, excitedly. I then asked, out of curiosity, "Have you been a Mistress before?"

She nodded, as she revealed, "I have been both a submissive to a very strong-willed dominant and a Mistress to a few submissive girls and women."

"A switch," I said, a term I'd learned from my lesbian reading.

"Yes, I see myself as a sexual chameleon, able to become whatever my partner needs," she said, sounding so mature and sexy while saying it.

"I'm not sure I'm anything but submissive."

"I don't know," she responded. "I mean you took control briefly when you pushed me on my back and sat on my face."

"I guess I did," I said.

"But there's no doubt your main persona is submissive," she said. "You're a pleaser."

"Always have been in work, family life and in the bedroom," I agreed.

"It's a role society creates for us," she said, so mature for her age. "And it's one we need to continue to work hard to break."

"Easier said than done," I said, knowing I had played my stereotypical role for years and only broken out of the humdrum life I was living through blackmail.

"Definitely," she agreed. "But that doesn't mean it doesn't have to be done."

"So you're a feminist?" I playfully teased.

"A sexual feminist for sure," she said. "My Mistress trained me to be a strong advocate for women, especially women who couldn't speak up for themselves."

"She sounds fascinating," I said, trying to imagine what this woman would look like.

"If all goes well maybe you can meet her one day," she said, before she ordered, abruptly breaking the mood, "On all fours, my pet."

Being called 'pet' instantly made me feel even more at home. I indeed wanted to be her pet and being on all fours was the ultimate submissive pet position.

I got into position, as I replied in true submissive mode, "Yes, Mistress."

She continued, as she kept up our conversation while ordering me around, "She is the most amazing woman I have ever met. She is a very powerful woman and she is changing the world every day."

"I'd love to meet her," I said, fascinated by Anastasia's vague description.

"And I imagine she would love to meet you," she added.

"Really?" I asked, as I felt her parting my ass cheeks.

"Oh yes," she said, "she would love to mold you into the perfect lesbian submissive."

"I'd love that," I said, wondering if I would be okay only being with women. I mean my experiences with men have not ended well, but God did I love a hard, real cock pounding into me. Sure a sex toy is nice, but it doesn't compare to the real thing.

"I know you would," she said, as I felt her tongue on my asshole.

"Oh, my," I said, surprised by the sudden wet sensation.

"I love eating an ass," she said, something I can say had never crossed my mind. She asked, as her tongue swirled around my rosebud, "Do you like it?"

I hadn't had time to process whether I liked it yet, as I tried to process what was happening. I answered honestly, "It's unique."

"Unique good or unique bad?" she asked, even as she kept licking my butt.

"Definitely good; weird, but good," I answered, that seeming to be the most accurate way to describe it.

"The first step to first-time anal is to loosen up your ass," she said. "It's not used to things going into it and needs to be trained to allow that."

"Okay, sensei," I joked.

She laughed too, parodying the Karate Kid, "Lick on, lick off."

"It is strangely relaxing," I mused, as she kept pleasuring my ass.

"This will make it even better," she said, as her hand went to my pussy.

"Oh yes, it does," I moaned, as I was suddenly getting multiple attention in two separate, as I was learning, erogenous zones.

"Eventually your ass will easily take a nice cock in it," she said, "but not until it is trained. And to be trained, you must be relaxed."

"And horny?" I asked, my pussy getting wet once again.

"And definitely horny," she agreed.

As she continued licking my ass, her tongue almost seeming to try and break through my tight one-way defense, I reached back and caressed her head, wanting to let her know I was enjoying her attentions.

"Ooooh," she said. "How did I forget?"

"Forget what?" I asked, as she moved away from me.

"Our Fifty Shades piece," she smiled, as she moved to her duffle bag.

"Rope?" I asked.

"Maybe next time," she said, as she pulled out a pair of handcuffs and walked back to me.

"Oh, I've never been handcuffed," I said, finding the idea of being helpless exciting.

"Well, another thing to check off your bucket list," she smiled, as she moved to the bed.

"Check," I agreed, as she handcuffed my hands together in front of me. It didn't leave me helpless, but I wouldn't be able to defend my bottom against anything.

"I hope to check off several things for you," she smiled, kissing me once, before returning to my ass. She resumed licking and eating my ass as she asked, "was this on your list?"

"It is now?" I joked.

After a couple more minutes of concentrated ass eating, she said, as she moved away, "Now let's go to stage two."

"And what is that?" I asked curious.

"Gradual gaping," she replied.

Gaping was a term I recognized from some porn stories where a girl was usually ass fucked really hard... usually by a thick black cock.

"I see," I said, as I watched her get off the bed and go to her duffle bag. She returned a moment later with not one, but two sex toys and a bottle which I assumed was lube. "What all do you have in that bag?" I asked.

"A plethora of toys for your pleasure," she responded, as she grabbed my hips and pulled me closer to the end of the bed.

"I like being manhandled," I smiled, looking back at her.

"Good to know," she winked, as she grabbed the lube and poured some between my ass cheeks.

"That's warm," I said, surprised.

"Good lube is critical," she said, as she surprised me again by then pouring some on her finger and moving it to my ass. I'd been expecting her to use a toy on me next.

"Good to know," I said this time, as I felt her finger poking my rosebud.

"You have a really tight back door," she said.

"It's been a one-way exit for over forty years," I joked, before adding, "except for a couple of brief wrong way collisions."

"Well, it will soon flow easily with two-way traffic," she said, as I felt a push and then a finger entering my ass.

"Ooooooh," I moaned, just a slight bit of discomfort at having something in there.

"Gaping is a process best done slowly," she explained, as I felt her finger moving around inside me, as if searching for something.

"Okay," I said, just enjoying the slow burn inside me. A finger in my ass wasn't really pleasurable, nor was it uncomfortable, yet I was enjoying it.

"I'm using my finger to open you up," she explained. "My cock is a lot bigger than my finger."

"I hope so," I joked.

"Fuck, you have a great ass," she said.

"Even with a finger in it," I joked.

"Probably would look even better with two fingers," she responded, as I felt her pull her finger out and then try to push two inside me. She then paused, "Oops, need more lube."

"And a crowbar," I joked, wondering how two fingers could fit in my tight ass.

"Or a lot of lube," she said, as more lube was poured between my ass cheeks.

After a moment of rubbing my rosebud with lube, she asked, "Ready?"

"I trust you," I answered.

"Good," she said, and I felt my ass widened as two fingers rather easily slipped inside.

"Oh my," I whimpered, the pain a bit sharper with a second finger. Like the first time, she wiggled her fingers inside me as I felt my ass gape.

"Your ass is accepting the gaping rather easily," she said. "Have you really never had anything else in this ass?"

"Only the tip of a cock a couple times long ago in college," I answered, "which had its invitation revoked quite soon," the pain still there as she widened me... although not intense.

"I plan to get a lot more than just the cock head in," she said, as she began pumping her two fingers in and out, while another finger teased my pussy, "and soon you'll be extending your welcome mat quite eagerly."

"That feels good," I said. "Weird good, but good."

"That's the plan," she said. "To make your ass want more, and to make you want more."

"I want to be your ass slut, Anastasia," I moaned.

"Don't you mean, Mistress Anastasia?" she corrected, as she kept fingering me.

"Sorry, yes, Mistress Anastasia," I corrected, as she finger banged my ass.

She then pulled her fingers out, stood up and grabbed the toys. "Ever been double penetrated?"

"Another unfulfilled fantasy," I admitted.

"Another first tonight then," she said, as I felt her hand reaching between my legs from behind and a cold dildo rubbed between my pussy lips.

"Oh, that is cold," I whined.

"Well warm it up then," she said, as she slid it deep inside me.

"Okaaaaaaay!" I moaned, not that I had any choice, being handcuffed and all.

She pumped the dildo in and out of me for a few seconds even as I felt another toy, one that was vibrating, poking my ass.

"Get ready for your first dp," she said, as I felt the toy in my ass slowly break through, the vibrations adding to the strangeness of the moment.

There was a slight pain.

There was a great pleasure.

And as the vibe went deeper into my ass I felt so full!

"Oh God," I said, the pleasure greatly overcompensating for the pain.

"You're liking this?" she asked.

"It's so weird and so good," I admitted.

"You look pretty hot with toys in your two holes," she said.

I moaned, "Too bad there's nothing to get me air tight." The air tight, filled with three cocks, fantasy still one of my biggest unfulfilled ones even after my six kinky days.

"I'll keep that in mind," she said, as she began moving both toys in and out of my two holes simultaneously.

"Oh my God!" I moaned, as the toys moved in and out of me. The dildo in my cunt filled me completely, while the toy vibrating in my ass enhanced the pleasure.

It made me wonder what a real pair of cocks would feel like moving in and out of me.