Blackmailed Ch. 01

Story Info
Judith get drunk, gets laid, and gets in serious trouble.
3.7k words
4.34
37.7k
51

Part 1 of the 4 part series

Updated 06/16/2023
Created 05/05/2023
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Prologue

I could feel the grin spreading across my face. I thought the message was direct and to the point. The pictures told the story anyway. I clicked on the little box on the screen so that the picture would be covered by the message except for the edges, and went into the bathroom to brush my teeth. She was snoring, not loudly, kind of a cute little purr. She was drooling too which most certainly was not cute. "Oh well," I thought, "she had a hard night and deserved her rest." I left her there on the motel room bed, thinking that I was going to have fun with this one.

Chapter One

I was aware of my head, roughly twice its normal size. As I lay there, waking up, feeling the hangover, I tried to get oriented. There was a little rush of adrenaline as it came back to me.

The conference had started, as all conferences do, with a brief afternoon meeting and then a break for the opening night reception. It had been a free bar and I was tired, and a screwdriver sounded too good to pass up. I had met Daniel a few times before. For all of the big crowds that Glenn Beck could draw, the true Tea Party group was still a fairly small family.

I was flattered when he asked if he could join me. At 52 I no longer draw the wolf whistles I once did, and attention from a handsome, bright 20-something was a pleasant change. I'm not particularly vain, but, well, it was flattering.

We talked of politics mostly, how the campaigns would go, who was working for whom, that sort of "inside baseball" talk. Before I knew it I had finished my third screwdriver and was starving. We walked across the hotel lobby to the restaurant and continued our conversation over steak sandwiches and beer.

I should have known better, but when he suggested a nightcap I said okay.

A nightcap turned into two, and then three, and before I knew it I was drunk. Not stumbling, falling down, puke-on-your-shoes drunk, but definitely and clearly drunk.

Inhibition destroying drunk.

And when he kissed me I didn't even think of David at home, I kissed him back. There was something deliciously naughty about doing it, and I liked it.

I leaned against him heavily as we walked to the elevator and giggled as I handed him my room keycard and said "Sheventeen thirty shix."

She was a cute drunk. And damn but she was attractive. I had always had a thing for "older women," and Judith was precisely my type. Her normally carefully coiffed hair was a bit flyaway and she was a bit unsteady on her feet. Okay, she was a LOT unsteady on her feet, just like I like my women. When I bent and kissed her, her arms went around my neck as I had known they would, and her mouth was eager under mine. "We'll see just how eager," I thought, as I broke the kiss and led her toward the elevators.

I had an instant of hesitation when he slid the keycard through the slot and I heard the solid click of the door unlocking.

"Judith," I thought, "you can't do this. Jesus, you're a married woman with three kids for Christ's sake."

But it had been SO long since David had shown any interest. God, it's like if I wasn't golf or work I was invisible. I felt lonely and, well, let's be honest, BOB can only do so much.

Oh, you don't know BOB? My Battery Operated Boyfriend. Well, he's always there for me but not a very good conversationalist, you know? And he never even kisses me.

I won't make excuses, though. I was flattered and drunk and horny, it really is just that simple. So when we got into the room I took a deep breath, told my conscience to shut the fuck up, turned, threw my arms around his neck, and kissed him.

And God he was a good kisser. His hands were up and down my back and he knew just how hard to press. Mostly, though, it was his lips. They fit mine perfectly and when his tongue traced the outline of my lips I felt a sudden rush deep in my belly that I hadn't felt for years.

"Jesus," I thought, "did she just cum? It smells like it. That little mewing sound she made sure felt like it. Oh, Judith, you and I are going to have so much fun.

I broke the kiss and pushed him away, holding him at arm's length.

"Daniel," I said, "I'm nervous. I've never done anything like this before."

"Don't worry, Judith," he said, and I liked very much that he didn't try to shorten my name to Judy.

He pushed me even farther away, looked at me speculatively for a second, and then said, "Come on."

"Where do you think we're going?" I asked.

"The balcony," he said, taking my hand and leading me across the room to the sliding doors that opened onto the postage stamp-sized balcony outside of my seventeenth-floor room.

The view was pretty spectacular from there, the city spread out before us, the lights bright, almost hypnotic. I watched, fascinated, as he pulled a little flat oval box from his pocket. He twisted the top and a little tube popped up, obviously spring-loaded. As I continued watching he pulled the tube out, looking like a cigarette, and pushed the end into the hole on the other side of his little magic box. He took a cheap Bic lighter out of his pocket and I smelled the pleasant burnt-leaf scent of marijuana, something I hadn't smelled since college.

He did the hissing deep inhale of a seasoned pot smoker and then pushed the end of the tube back into his little box and handed it to me.

"My one-hitter," he said, smoke puffing out, "never leave home without it."

So I took the tube and the lighter and for the first time in three decades took a hit of marijuana. Well, I hissed and coughed anyway.

We laughed together as he reloaded the one-hitter and my second try was better. I hissed the smoke deep into my lungs and held it this time, smiling up at him.

"Jesus," I said, as the pot hit me quickly and hard, "this is better than my college days."

He grinned and said, "The wonders of legalization. Price is down and quality is WAY up," as he reloaded, took a hit, reloaded, and offered it to me.

We did three hits that way and the itching behind my eyes told me I was beyond buzzed to high.

"That's right," I thought, "drunk and stoned, just like I like my women. On Judith, you are in for an interesting life."

I stretched, my back arched and my arms straight up over my head, and heard the little click of a cellphone camera. When I turned my head I saw him looking at the screen of his cellphone as he pointed it at me.

"DANIEL!" I sort of half yelled.

"Don't worry," he said, laughing, "just for fun."

And I was flattered, a bad combination along with the alcohol and pot. This handsome young man was interested.

So I smiled, what I hoped was a coquettish smile, and reached up slowly and dramatically for the top button of my blouse.

"That's right, Judith," he said, and the cell phone clicked quickly three times.

I think I actually felt the last of my inhibitions leave me about the time I tugged the blouse free from my skirt and, the last button undone, opened it, my conservative white bra on display, smiling broadly.

"Oh yeah," I thought, "get those tits out."

"Don't stop now," he said and I giggled and reached behind to unhook my bra.

I had one tiny instant of hesitation, holding the bra on with my arms held tight against my ribs. Looking back, I suppose that was my last chance to avoid what was to come.

"Come on baby," he said, "tits in the wind," and I thought, "Fuck it," and pulled the bra-free. I met his eyes, giggled, okay, probably a little hysterically, and dropped it over the edge. We both laughed as we watched it flutter to the sidewalk below, jerking back onto the balcony when someone on the sidewalk looked up. We were giggling like a couple of school kids.

"Nice tits," he said.

"These old saggy things?" I asked, holding them up, rolling my nipples, hard in the cool air, between my thumbs and forefingers.

"Those lovely things," he said, laughing, and the cell phone clicking away.

"Now the rest," he said, and the thing is, by then, I didn't want to stop.

I found the button and zipper of my skirt and dropped it to pool at my feet. I felt slutty. I felt naked. I felt wanton, standing in the cool night air in only my pantyhose, panties, and pumps. Well, I still had on my necklace and watch and wedding ring, but I don't think that really counts, does it?

"Go on," he said and his voice was so soft, almost hypnotic, that I didn't even think of saying "no."

Now there is no way to take off a pair of pantyhose gracefully, every woman knows that. But I hit new levels of awkwardness when I managed to fall on my ass as I worked my shoe off.

He made no effort to help but, rather, stood over me, the cell phone clicking relentlessly.

I lay there, flat on my back, giggling helplessly for a while, until I managed to get myself back together. Then I sat, scooted back until my back was against the wall, and got the damn shoes off. For an instant, the image flashed through my mind of the shoes falling to the sidewalk below but I didn't do that. The pantyhose were ruined and they did join the bra on the sidewalk although it took two throws, the second after I crawled to the edge of the parapet where the pantyhose hadn't quite made it over on the first one.

I stood then, in just my panties, and when he reached out, his finger pointed down and did the twirling thing, the universal symbol for "turn around," I turned, slowly, putting a wiggle in my skinny ass. The second time around I laced my fingers behind my head, putting my small breasts on display to their best advantage, and moved my feet until they were a little over shoulder width apart.

"All of it now," he said and I didn't hesitate. I pushed the panties down and kicked them over the parapet.

I was enjoying this at the same time that I was nervous and just a little ashamed.

My nipples were so hard they ached and the cool night air was getting to me.

"Gotta pee," I said, and went back through the room to the bathroom.

I sat and peed, swallowing around an incipient wave of nausea, but eventually got my stomach to calm down.

As I sat there I broke out in a cold sweat and that seemed to break my mood.

I had plenty of pictures, but I wasn't done with this cunt yet. I called room service, ordered up a pitcher of Margaritas, charged to her room of course, and waited. She was still in the bathroom when the bellboy brought the drinks. I tipped him generously on her room number, poured a drink for her, I had enough, and walked into the bathroom.

"Jesus, Daniel," I said as he strolled in.

"Spread your legs or get up," he said, that damn infectious grin on his face, "'cause I gotta go."

"DANIEL!" I said but as I watched him unbutton and unzip I realized he was serious so I stood, unwiped and feeling perfectly naughty as I sort of leaned against the vanity and watched him.

It's funny, well, and probably sad on some level, but in my 30 years of marriage, I had never seen my husband pee. He took a drink, handed me the glass, and got his dick out.

Okay, I stared. He was bigger than David and, well, I was drunk.

He laughed and said, "Wanna aim it?"

I giggled and moved behind him, reached around, and took him in my hand.

"Be careful, Judith," he said, "'cause you're cleaning up any misses."

I bent to look around his arm to see what I was doing. I missed at first but got him aimed and heard the splashing as he peed. I don't know that I ever felt more deliciously naughty than I did right then.

When he was finished, and I watched as he seemed to push out the last two or three squirts, he said, "Three shakes now. More than that and you're playing with it."

After a brief hesitation, he added, "Not that I'd mind."

So I shook it, a carefully counted three times, feeling warm drops on the web of my thumb and, oddly, not minding.

"I warned you," he said, and there was a new tone in his voice, "that you'd clean up any messes, so down on your hands and knees Judith. You missed."

When I hesitated he snapped, "NOW!" kind of scaring me but then he flashed that smile. "You're not going to break a deal, are you?" he added.

"Oh, Judith," I thought, "that was your last chance honey. You can be broken and I'm just the guy to do it."

So I got to my knees, pulled off a yard of toilet paper, folded it into a pad, and wiped the floor where I had missed. A second pad and I wiped the side of the bowl.

When I turned he had his cock out and was waving it.

"Since you're down there already," he said.

"Daniel," I started but he interrupted me.

"Let's get that pretty mouth busy, Judith, we'll talk later," he said.

It was demeaning, It was debasing. I was on my knees in the bathroom of a motel room, naked, while this young man I knew only casually, was waving his dick in my face.

And my big problem was, I was drunk enough to do it.

I opened my mouth and took him in.

I heard the artificial clicks of the camera function on his cell phone and when I looked up he said, "Smile."

And I did. Well, I smiled as well as a woman can with a mouth full of cock.

I felt naughty and slutty and dirty. And I liked all of it. I knew it was the alcohol and the pot at work, and honestly, I just didn't care. It had been a while since I had felt like a sexual being and I was wallowing in it.

I was surprised, almost hurt, when he pulled me off of that beautiful cock.

"That's enough of that for now," he said, "you're too photogenic to pass up."

For the next hour or so, while we finished the Margaritas and another joint, he, well, he "directed" me.

That little clicking sound followed me as I posed. Then he had me turn my back, and grab my ankles for several seconds while that "click, click, click" kept going.

He had me spread my cheeks while bent over like that, then bend far enough so I could look at him between my legs.

He had me lay on my back, pull my knees up until they touched my nipples, and then open myself, demanding I open myself wider until it hurt.

He had me on all fours, lapping beer from a dish on the floor.

He had me masturbate while he watched and that camera kept clicking away.

And I was enjoying myself.

Finally, he took me. I was on my back and he had my ankles in his hands, holding my legs apart, while he fucked me. This wasn't anything even remotely close to "making love." This was raw fucking and I was loving it too.

I cried out "harder" loud enough that he covered my face with a pillow.

When I came, something a man hadn't done for me in months, he twisted my nipples hard enough to leave them bruised.

But I was exhausted by then and when I felt his ejaculation fill me to overflowing I barely managed a "Thank you" before I fell asleep.

Honestly, maybe "passed out" is a better word.

I woke, knowing I was going to be sick and that I had to pee. After rolling out of bed, almost falling, and stumbling to the bathroom on weak legs, I barely made it before my rebelling stomach emptied itself explosively.

I had the random thought, as a second wave hit, "So THAT's what they mean by projectile vomiting." I was hanging onto the bowl helplessly as I threw up in waves. I felt the warm wetness and realized my bladder control had failed too, but I couldn't stop either end.

I know, in my head, that it wasn't hours that I was in there, my head in the toilet and my knees in a puddle of piss, and before it was over, worse. But it sure felt like that.

Eventually, my stomach was empty and I was reduced to dry heaves. That odd little corner of my mind was thinking, "Jesus, this hurts even worse than the puking." My bladder was empty and my nose told me that there was more than urine on the floor.

I was afraid to look as I hung onto the comforting coolness of the porcelain trying to get my breathing back to normal and my digestive system working in the right direction.

I used most of the roll of toilet paper, flushing the toilet frequently, to clean up the mess on the floor. At one point I had to stop and throw up again, straining so hard it made the intercostal muscles between my ribs cramp. I swear, once, I heard two ribs click together.

I was still pretty drunk and giggled a little hysterically as I thought, "Now that's a tidy little ladylike turd," as I picked up that part of the mess. I got the giggles as I watched it swirl down the toilet.

Feeling almost human, I turned on the water in the bathtub and started it running through the shower head. I caught a chill and shivered while I waited for it to start running hot.

In the shower I just stood, letting the hot water sluice over me, for a long time. Eventually, I gathered my strength and washed my face. I used the cheap motel shampoo and when I felt the thick mats in my hair my memory flashed back to being on all fours on the bed while Daniel, on his knees, twisted my hair and gagged me with his cock before finally pulling out and cumming in my hair and on my face.

I shuddered and shampooed again.

The conditioner was just as cheap and I felt like I was working Vaseline into my hair, but at least it was clean.

When I started on my body I groaned as I washed my breasts, wondering if they were bruised as I remembered crying out when he mauled them. My butt was sore too and I could remember being, not exactly "spanked," but him slapping my ass. But when I ran the little bar of soap up my gluteal crease, the crack of my ass, I yelped when I got to my anus and the memory of him taking me anally, holding my face buried in the pillow to muffle my yells flashed before me.

Finally, reasonably clean and almost fully sober I turned the water off and stood in the tub as I dried the soles of my feet and my calves, almost falling twice in the process, and stepped out on the thin bath mat to finish.

The woman I saw in the mirror looked, as my mother might have said, like she had been "rode hard and put up wet."

There were five circular bruises on each of my breasts.

My eyes were red still, residual from the pot I thought.

My mons and my labia were red and swollen.

Yeah, I looked rough.

I finished toweling dry, drank two glasses of water from the little plastic glasses the motel provided, gathered my courage, and went into the bedroom to get dressed.

He was gone, of course, and I half expected to see some money left on the dresser, I felt that cheap.

There on the little desk, my laptop was open and I could see the edges of what appeared to be a picture overlaid by a message.

I read the message and ran into the bathroom for another bout of vomiting.

Judith: it read.

Thanks for last night and for many times to come.

So you know, I dumped your email contact list onto my phone and, of course, I have the pictures, copies are on your laptop too for your entertainment.

Don't you worry though, sweet cheeks. As long as you do what you're told I won't send them to everyone on that list.

Enjoy the rest of the conference. I need to get rolling but don't you worry that pretty head. I'll be in touch.

D

My belly empty again I sat at the desk, still naked, and started flipping through those damn pictures.

Jesus, if he passed these out, then everyone I know would see things only my gynecologist had ever seen, and even then I had been embarrassed.

I realized as I looked, it was like a bad car wreck, I couldn't look away.

"Well," I said aloud. "you, Judith, have really screwed the pooch this time."

I took a deep breath, gathered myself together, got dressed, and went down to the conference.

I had trouble concentrating.

And I didn't see Daniel there.

In fact, I didn't see or hear from him for almost a month.

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HighBrowHighBrow7 months ago

First vaguely realistic version of Femsom agitprop blackmail I have seen so far. Great start.

AnonymousAnonymous12 months ago

Well, good start to hopefully many chapters of her adventures. One commented that he should have some buddies come over to help him. That is for a couple of chapters after he uses her for his pleasure and her humiliation. After he uses her for awhile he could make her attend other conferences as a party favor, go to frat parties for a weekend, attend some gloryhole sex shops, etc. There are so many options to explore. Good start.

AnonymousAnonymous12 months ago

She had better get in contact with somebody that could put a hurting, or much worse, on that asshole

AnonymousAnonymous12 months ago

Great story……it’s not a big deal. Blackmailers are just bullies. She needs to come clean with hubby then make a plan. Hopefully hubby isn’t a big pussy & knows a couple bad asses & they pay this creep a little visit.

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