Frustrated Milf Ch. 06

Story Info
Peggy meets Dennis's father.
3.8k words
4.52
10.6k
9

Part 6 of the 8 part series

Updated 04/25/2024
Created 04/28/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
hoover789
hoover789
307 Followers

Milf6

I don't know how long I passed out. But when I came too, I was on the bed with Dennis fucking me doggy style while spanking my sore ass. As I became more aware of what was happening, I realized somebody was taking a video of me being fucked.

I was a mess; my hair was plastered on my face with drying cum. My makeup was smeared, but I still grunted with pleasure at each thrust.

"Hey, she's awake; somebody get a dick in her mouth."

They were all laughing when I felt a stiff cock jabbing at my tender lips. I meekly opened my mouth and welcomed the invasion. I ran my tongue up and down his slippery cock, but he was intent on throat fucking me. I didn't fight him and tried to relax; it's good I was drunk.

I was somewhat aware of Dennis squirting his cum in me. When I felt a bigger dick entering my puckered ass. I started to struggle. Spitting out the dick in my mouth, I screamed as loud as I could.

"STOP IT YOU'RE KILLING ME!"

"Fuck her ass, make her scream."

Somebody yelled as I collapsed in tears. The guy in my mouth took advantage of my distraction and jerked off on my face adding to the mess.

At this point, I didn't care what happened to me. I think it was Henry hammering my ass, but it didn't matter who it was. I shuddered through another orgasm.

I couldn't believe the stamina these guys had. It was two o'clock Saturday morning, and they still wanted more. Finally, an hour later, they started getting dressed.

"That was fun, guys; let's fuck her tomorrow night."

Hearing that, I started to gag and threw up in the trash can a mixture of cum and spit. After they left, Dennis sat in a chair with a beer.

"You're a good slut." He said, "Come here and clean this up. Pointing to some cum on the nightstand.

"Please don't make me do that. I'm so sick," I whined. He grabbed me by the back of my neck and pushed my face into the pool of cum and spit.

"Start licking, cunt."

My head was spinning; if I could do this, maybe he would leave. Still in my stockings and heels, I gingerly licked up the cold congealed cum. Controlling my urge to spit up again, I licked it clean.

Sitting back, I asked,

"Is that good enough, Dennis?"

"Yeah, good job; I'm going to go now. I'll let you know when I'll be back."

I kicked off my heels and stumbled into the bathroom for a shower.

I slept till noon and dragged myself out to the kitchen. I needed food in my stomach.

My Saturday was a waste. Sitting on the couch, feeling sorry for myself, I could hardly move. Every part of my body ached.

The day went by without a word from Dennis. Finally, at ten o'clock, my phone rang.

Please, God, no, not this late. I can't do it. I shouldn't have answered, but I did.

"Have you fully recovered? My sweet."

I could just imagine him smirking as he said that.

"You're going to be disappointed. I have to take my mother to a funeral out of town, so I'll be gone for a couple of days. But I'll be watching you."

I wished him well, trying to conceal the joy in my voice. After he hung up, I jumped into bed for a good night's sleep.

I slept till ten feeling much better. I busied myself and did some online shopping. I was having a normal Sunday without any pressure to perform.

Monday morning came too quickly. Once in a while, I felt like wearing dress slacks. But I didn't dare with Dennis watching me all the time. I wasn't sure if he could still watch me from out of town, but I wouldn't take any chances.

I chose a black and white checked mini skirt that ended well above my knees. My white blouse was tight across my chest, showing my black bra, pulling my off-black stockings as high up as possible. To give me a little protection before my stocking tops showed. Feeling good about myself, I headed for work.

Men are so predictable. Take, for example, no matter what time I arrive at work; there always seems to be some guys talking or checking their cars or doing anything so they can see me get out of my car. And to be truthful, I always give them a little show. Today I opened my door, swung my legs out, and checked my nylons, pausing long enough to ensure my skirt was up to my garter clasps before pulling my hem down. It's funny; as soon as I walked into work, they all followed me to watch my wiggling ass. Just a coincidence; I don't think so.

The day was a typical Monday. The only thing that saved me was my memories of Friday night. I had to stop thinking about it. I could feel myself getting wet.

I stayed a little late to catch up. When I walked out, there was a single car near me. The windows were tinted, so I couldn't tell if someone was in it. This was one of those times I wished I was in flat shoes. The walkway was cobblestones, and I had to take small steps, causing my skirt to ride up and my boobs to sway. I made it to my car, relieved it started, and as I drove away, I saw the other car start following me. The car seemed slightly familiar, but I couldn't place it. I drove slowly, but it made no move to pass me. As I turned down my street, it was still there. I got my phone out as the car parked behind me and tapped the horn. The door opened, and a man got out smiling.

It was like someone hit me in the stomach; it was Dennis's father. He strode up to my door and opened it, and his eyes went straight to my legs and my exposed stockings. On my drive home, I was so worried about who was following me that I forgot how short my dress was. The hem was above my stocking tops, exposing my garter straps and silver clasps.

I blushed red as he introduced himself as Dennis's dad, "Brian," but he never took his eyes off my legs. I stood up, tugging my wayward skirt into place.

"It's really nice to meet you, I would invite you in, Brian, but I've got a lot to do."

The smile left his face.

"I've only got one question: why did you supply booze to nineteen-year-olds for your party?" He took my arm, getting close to my face.

"Why don't we talk inside? Or do you want me to call the police?"

I unlocked the door.

Once inside, he sat down; I was standing before him like a student in front of the principal.

"That's quite an outfit you have on. I can see why Dennis likes you. Why don't you get more comfortable."

I knew what he wanted but played dumb.

"I'm fine, thank you."

He was easily six feet tall, and when he stood up, it made me realize how short I was. He seemed to take up the whole room.

"After what you did with Dennis and his friends, I own you. Now take off your clothes. Or would you like to see the video of the party? we could post it if you want.?"

"I'll do what you want," I whispered.

He was very calm, and there was no question in his voice. I knew how crazy his son was; he had to get the meanness from somebody.

I unzipped my skirt and let it fall to the floor. I started unbuttoning my blouse. My whole body was trembling; I feared he would tear it off. Finally, I removed it and stood before him in my underwear. My garters tugging my stockings fully expanded tops. He turned me around to inspect me like a piece of meat. I prayed he wouldn't finger my cunt; I was just about dripping.

"I didn't know women wore stockings in real life; I like it. it makes you look like a whore."

Mt face was burning. How could he talk to me like that?

He reached out and squeezed my tits. I winced from the pain but didn't cry out. He pulled my cups down, and my boobs sprang out. He immediately covered them in kisses biting my hard nubs. I put my head back and moaned as he mauled my swollen tits. He was alternating, sucking on my nipples and slapping my boobs. I wanted him to leave but was in heaven from the pain.

"You're one hot little tramp; now get on your knees."

I had no choice. Purely out of fear, I complied, dropping to my knees. I unbuckled his pants and fished his growing cock out.

It wasn't that long, but it was definitely fatter than most as I stretched my full lips around it. I was struggling to get it in my mouth. There was a ring of spit and pre cum on my lips. Then like most guys, he grabbed both sides of my head and started to face fuck me. I began to panic. His thrusting was making it impossible to breathe. I looked up at him with wide eyes, tears rolling down my cheeks.

He was chuckling,

"Looks like you're having trouble with a real man's cock."

He pulled his dick out, smacking my face while I gasped for air.

"Please, Brian, no more. Jerk off on my face if you want. But I'm going to pass out if you hold my head again."

He pulled my hair back, forcing my head up as he plunged his dick back into my mouth.

"We're just getting started, Peggy. Open wide."

I was beating him with my fists but to no avail. He held my head tightly, so I could not move my tongue. I have never had an experience like this.

Finally, his dick erupted in my mouth. I was coughing and gagging, trying not to drown in cum. It was running out of my nose and mouth. He stood over me, grinning while slapping my face with his dick.

I collapsed on the floor, gagging up cum. He was as cruel as his son. He pulled on my hair, making me look at him.

"I've got to go, so this will be our little secret. Maybe I'll see you soon."

I forced myself to my feet. I felt like he had punched me in the mouth; my lips were sore. What a mess I was in. Between father and son, I think I would do anything they wanted.

We were swamped at work, which took my mind off my troubles. Dennis was back playing mind games with me. He called me Thursday morning to say that there would be workers upgrading the phone lines and to be sure that when they were in my office, I was to give them a leg show.

I knew he would be watching. I had a dark blue pinstripe skirt, sheer glossy blue stockings, and a white starched blouse. With four-inch pencil-thin blue heels.

Two young guys from the phone contractor arrived at about eleven. They were in their early twenties. I guess to them, I looked like a boss lady from porn films. They couldn't look me in the eye but spent enough time looking at my legs and boobs.

They were working in the corner behind me; I casually swung my chair out to get to a filing cabinet. In the process, I was hiking my skirt up to my silver garter clasps. Out of the corner of my eye, I saw him elbowing his buddy to look. Just then, my phone rang; it was Dennis,

"Very good, you really do like to tease. Well, you're not done yet. Keep your skirt up and walk to your copier."

"Please, Dennis, don't make me do that. I'm so embarrassed."

"You've been told, NOW DO IT!" He hung up.

I knew he would be watching.

I ensured my stocking tops were exposed, stood up, and walked to my copier. I acted like it was out of paper and bent down, hiking my skirt higher. I knew they were taking it all in, but I couldn't look them in the eye. My pussy was aching. I was praying these guys would rip my clothes off and fuck me senseless. But no such luck.

I spent a few minutes there and then quickly returned to my desk. I wouldn't dare pull my skirt down. They left about two. I later found out they were in the other offices for only fifteen minutes.

I heard from Dennis the following day. He called to say he would be over at seven for a talk. I wondered what that meant, and he didn't say if somebody else would be with him.

I chose a black cocktail dress and went with a new corset I had just bought. He liked me wearing heavy makeup, so I went with black eye shadow and fake eyelashes with hoop earrings.

I was nervous as I could be. With guys like Dennis, the slightest thing would set them off. I downed two shots of whiskey. I needed to be drunk, not unconscious. He arrived early, carrying a small duffel bag. I didn't dare ask what was in it.

He asked for a beer while I gulped another shot. I was feeling pretty mellow with a slight spin to the room. Dennis sat on the couch. He motioned for me to sit on the floor next to his knees. He patted my head.

"You were a bad girl the other day. You questioned my order to walk to your copier. If we are to have a traditional relationship, you have to obey me."

I was too scared to say anything but,

"I'm sorry."

"It's too late for that."

He stood up, taking my hand and pulling me up. He stood behind me and unzipped my dress, letting it fall to the floor. I could hear him open his bag. After removing his clothes, he told me to reach behind my back and grab his dick. His dick was already hard as I started to massage it.

Then I heard a sound that scared me to death--the click of handcuffs and then cold metal on my wrists.

I started to shake.

"Please take them off. I'll do anything you want."

"You will do anything no matter what."

He sat back down, and I stood before him in heels, stockings, and underwear.

"Bend over. I want to see your tits."

I bent at the waist, my tits thrusting out with my hands behind my back. I knew he couldn't resist slapping my boobs, I couldn't control myself, and I started to cry. He laughed, saying.

"We are just getting started."

He reached into the bag and took out a blindfold. My hair was in a French up sweep, so he had no problem putting it on me. I was so scared that I felt like I was going to pee myself.

I could hear him moving around; he grabbed the waistband of my panties and pulled them up the crack of my ass. He broke the silence.

"Peggy, were you a bad girl?"

"Yes, I was. Just please don't hurt me, please."

With no warning, I felt the sting of a leather crop strike my upturned ass.

"YEOW, STOP IT."

"Go ahead and scream; no one can hear you, as he rained blows to my rear. He stopped for a minute, thank God. My ass felt like it was on fire. I was sobbing.

" No more, no more, please, no more." I kept saying. I heard him leave the room and return shortly; he came up behind me and gently rubbed an ice cube over my sore butt. It felt like heaven.

"Thank you," I mumbled. As the fire subsided. I asked for another drink, and he tipped a glass to my lips. I gulped it down, trying to blur my predicament.

He took my arm, guided me to the couch, and sat me down beside him.

"Time to suck some cock, Peggy."

I didn't hesitate, leaning awkwardly, my mouth searching for his dick. The pain in my arms increased due to the angle. But I was able to capture my target and sucked intently, hoping to get this over with.

He put his hand on the back of my head, forcing his dick deeper. I was moaning, part passion, part pain.

I was running my tongue on his sensitive glans. He freed my tits from my corset and began torturing my nipples. My cunt was on fire; I needed a cock in me.

It's good he's young and couldn't last long. He held my head and tensed up, shooting cum down my throat. I couldn't swallow it all, with some dripping on his belly.

He popped his dick out of my mouth and forced my face into the cum.

"Lick it up, and do a good job."

I licked all over his stomach, afraid of what would happen if I missed any.

I felt him get up. I forced myself to sit up, unable to see. I was scared of what he might do. I could hear him in my kitchen as I sat there with cum dripping on my tits.

He came back into the living room humming, as happy as he could be.

"Do you want to watch a movie?"

Laughing hysterically at his joke.

"I'm sorry I forgot. Maybe we'll take it off soon."

I felt the rim of a glass touch my lips; it was whiskey; I gulped it down, hoping I would pass out.

Dennis pulled me up, walked me a few steps, and helped me into a straight-back chair.

"What are you going to do to me?" I whispered.

"Don't be worried. I don't want anything to happen to you, not just yet. There's a lot more I want to do. Now let's get pizza."

I was in my living room, in my underwear, handcuffed with a blindfold on. Waiting for a nineteen-year-old boy to play out his fantasies.

I began to panic. I was in full view of the front door. The pizza guy would see me like this.

"Dennis, please let me up before the delivery guy comes. I'm so embarrassed."

He came up behind the chair, kissing me on the neck. He reached around me, cupping my tender tits. my nipples sprung to attention.

"I'll lead you to the bedroom, but I'm not removing your blindfold.

I felt a metal chain brush my boobs, then a burst of pain. The bastard had put nipple clamps on me. I screamed. The pain was so intense. He tugged on the chain. I jumped to my feet, trying to get some relief. I stumbled after him in my heels. Once in the bedroom, I sat on the bed. My nipples were screaming.

"I think that was long enough for the first time." Dennis snickered.

As he released the clamps. I blubbered. "Please, no more. I'll do anything you want, just no more clamps."

"Careful what you wish for, Peggy."

He said as he unlocked one handcuff and pulled the blindfold down.

"Better tuck those tits back in. You're going to the door, and don't argue with me, or you'll have to blow him."

I stood up, blinking in the sudden light. I pulled my cups up, barely covering my nipples. I went into the bathroom. I had more cum on me than I thought.

I had just repaired my makeup and hair when I heard a knock at the door. I pulled up my nylons, the tops fully expanded.

"Can I at least put a robe on? No, now, get moving." I was prepared for some guy to gawk at me. But

as I opened the door, I nearly died. Instead of a guy, it was two college girls. They looked at me standing there in my corset, nylons, and heels. With one handcuff still attached and the nipple clamps draped around my neck.

They looked me over, giggling. I had to go back in for the money, giving them a view of my backside with my nylons pulled tight. I could hear them commenting on never wearing stockings to please a man. Dennis gave me the money and told me to invite them in when they got off.

"You're welcome to come back later?"

I said, casting my eyes down.

They looked at each other and burst out laughing.

"EWW That's gross, no thank you."

Dennis called out from the kitchen.

"Are you sure; Peggy's good at cunt lapping."

I was mortified as tears started rolling down my face. I closed the door; what had I become?

Dennis laughed at my tears, smacking my ass.

"Get in the bedroom.!" I hurried as quickly as my heels let me. All while trying to keep my tits in their cups.

Once in my bedroom, he grabbed my hair, pulling me onto my bed. Smacking my tits, he asked.

"Where do you want it?"

"My pussy, please, just don't hurt me."

All my pride was gone. Dennis was twenty years younger than me, and he was ordering me around like I was a cheap hooker.

I laid back on my bed. He took my panties off in one motion and proceeded to stick his tongue in my dripping slit. I wrapped my nylon-covered legs around his head. He was very talented. I must have cum three times from his probing tongue. My head was reeling from the whisky and the need I had to be used by men.

I was in a fog when I realized he was entering my wet cunt. Thankfully I was wet because he gave no warning, just plunging in. It's good he ate me out because there were no other preliminaries.

He gave me no mercy, grabbing my heels, pushing my legs back over my head, taking delight in my discomfort while ramming me nonstop on his way to cumming.

He pounded away, unmindful of my crying from the pain. He tensed up, squirting his cum deep in me.

"You're one tight cunt, Peggy. Tell me, was it good for you, too?" he snickered.

He got up and headed for the bathroom. I curled up, not wanting to move, cum dripping out of me.

He left without saying a word which was fine with me.

I had reached a low point in my life. I knew I would have to make a choice.

hoover789
hoover789
307 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
StrappySandalsStrappySandals5 months ago

Nipple clamps are a personal favorite... But Dennis is a creep!!!

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Beth's Disgrace Pt. 01 Uptight girl afraid the world will discover her kinks!in NonConsent/Reluctance
School Teacher Photo Shoot Young teacher's posing goes further.in Loving Wives
Ashamed, Blackmailed, Corrupted Ch. 01 Emily is blackmailed into a humiliating sexual encounter.in Fetish
Blackmail Psychology Ch. 01 The beginnings of a Ph.D. student being turned into a slut.in NonConsent/Reluctance
Taking Ownership of Emma Drunk truth or dare allows husbands friend to take control.in NonConsent/Reluctance
More Stories