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Frustrated Milf Ch 09

Frustrated Milf Ch 09

by hoover789
19 min read
4.5 (12100 views)
adultfiction

All the people in this story are over eighteen years old.

Frustrated Milf Ch.09

The rest of the week was a blur. I felt all alone. Ashley had called out sick, so I had no one to talk to at lunch. She had been out three days. I wanted to call her, but I didn't dare with Dennis monitoring my phone calls. I was trapped.

I used a company phone to call her, but it went straight to voice mail.

With Dennis watching my every move, I couldn't get away with much. Take today, for instance. I wore a tight black spandex dress that was one of his favorites. It was unforgiving, to say the least. When I was standing, it stopped above my knees, but, forget sitting; it rode up, exposing my stocking tops and garters. I'm not being paranoid about him watching me. Five minutes after I arrived this morning, my phone rang; it was Dennis telling me to sit sideways so he could see my legs. The problem was that sitting that way killed my back, but I had no choice.

Later that morning, Dennis stopped by my office and said he had to check my computer. I moved to get up, but he raised his hand.

"You can stay seated; I've got plenty of room,"

He crouched down, letting his hand rest on my leg. He squeezed my knee gently. I shuddered as his hand traveled higher.

"Dennis, not here."

I was trembling, scared of what he might do. He reached my stocking top and inched slowly higher until he lightly brushed my soft mound.

"Dennis, please stop. Someone will see us."

I involuntarily spread my legs slightly, giving him access to my needy pussy. He tickled my cunt very lightly; my mouth sagged open as my head lolled back.

"Oh, why are you doing this to me?"

He smiled, looking up at me.

"Because you're such a whore. Now beg me to fuck you and make me believe you."

I was on fire with just a light touch from him.

"Fuck me, I'm a dirty whore. Make me crawl; fuck me from behind. I'll do anything you want."

"How about pulling your dress up to your waist."

My dress was too tight to pull it any higher while sitting.

"I can't do it; my dress is too tight."

"Then stand up. I want to see your ass."

My office had glass on two sides so anyone in the hallway could see me. He stepped back, took my hand, and pulled me up. He had an evil smile on his face. I knew what he could do to me, and I surrendered.

My hands went to the bottom of my dress and pulled it slowly, exposing my stockings and my hot pink panties.

"Turn around, Peggy, and give me a show."

When my ass was facing him, he told me to stop and bend forward over my desk. He pulled my panties up the crack of my ass and worked his finger under my panties. He was teasing me with his hand, getting close to my pussy and then pulling away. I needed to cum; but he was content with making me beg.

His fingers finally touched my dripping cunt, I nearly exploded. I moved my body, trying to get his finger in me.

Then he abruptly stood up, leaving me withering on my desk. At that point, I would have let any guy with a hard dick pound me senseless.

I slipped down on the floor. Looking up at him, I debased myself further by begging him to fuck my mouth.

"Please let me suck your cock. You can cum in my mouth. I need it."

He walked toward the door, grinning.

"You better save some of that energy for the party tomorrow night.

"See you later."

He was laughing as he left my office.

I sat down and hunched forward, sliding my hand up my dress and rubbing my throbbing cunt, quickly bringing myself to an unsatisfactory orgasm.

It was almost quitting time when I saw Dennis coming toward my office. He walked in with a paper cup in his hand. He sat on the edge of my desk.

Looking at him, you would think he was a typical timid nerd. In reality, he was a domineering bastard who had no respect for women. He smiled at me, and my blood ran cold.

"I know you were frustrated when I left you this morning, so I brought you a present."

He extended the cup to me.

"When I got back to my office, I couldn't stop thinking about how much you like my cum. So I jerked off in this cup. Now drink it, or I'll pour it on your face."

I took the cup from him. My hands were shaking. The cup was over half full.

"Hurry up, don't spill any. You don't want me angry."

I brought the cup to my lips. It had a strong smell of musk.

I closed my eyes and drank the bitter cum.

"Open your mouth. I want to see it."

My mouth sagged open, his cum coating my tongue.

"Very good, Peggy, you may swallow."

I gagged almost immediately but swallowed it, getting a little on my chin.

He was standing over me.

"Good girl, but there's a little left. You know the rules; pour it on your nose and rub it on your cheeks."

Burning shamefully, I dripped the few drops left on my nose and spread the rest on my cheeks.

"See you tomorrow night."

I sat there, afraid to dry my face off. What's wrong with me? I was looking forward to being gangbanged by guys twenty years younger than me.

I could live with the fact if they just wanted to fuck me, but no, they wouldn't be happy until they humiliated me.

Taking a personal day off work on Friday did me good. I slept late, waking up as usual with my hands on my crotch. Dennis refused to tell me who would be there, and I knew with his look that I could only ask once. He wanted me to ask again, looking for a reason to slap my tits.

I dreaded facing Richard, who had started my cravings for younger guys.

I spent the day getting my nails done and my hair frosted, although there would be no lack of "Frosting" in my hair tonight. Dennis wanted me there at six o'clock, and I was so nervous I couldn't eat anything.

Dennis was very particular about what I was to wear.

He provided me with a black dress with buttons up the back. The front had a deep scoop neckline and spaghetti straps. He also provided me with a black push-up bra with a matching garter belt and panties. Four-inch heels and a black choker completed my outfit. I struggled with my ripe tits. The bra was one size smaller than I needed to help control my swaying boobs.

Before I left, I made a drink, downed it quickly, and then a second, I felt reasonably buzzed.

When I pulled up to his house, it seemed like a nice neighborhood. Sitting in my car, I teased up my hair and looked down at my legs, my stocking tops and garter clasps exposed. I was dressed like a whore; all this for that dirty creep. There were a lot of cars parked on the street; they couldn't all be for Dennis.

I started getting nervous. I was expecting maybe four guys at most, but a quick count revealed eight cars.

There is no way I could handle that many cocks.

I tried walking on my toes to prevent my heels from hitting the sidewalk. Tall hedges around the house provided some cover.

I could see into his living room. He was sitting on the couch reading something. There was nobody else with him. Carefully walking up to his front door, I was shaking. I knocked lightly.

"Come in."

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I opened the door and went inside. He stood up and smiled.

"So good of you to come over."

His tone was mocking me; I didn't have a choice. My head was buzzing from the drinks, and I would have to perform for him and his friends.

"Turn around. I want a good look at you. I like your choice of nylons. Hitch your dress up. I want to see more."

I pulled my dress up to my waist, blushing furiously.

"We're going to have fun with you tonight. There's not many women your age who would wear stockings for a bunch of horny twenty-year-old guys."

"May I lower my dress?"

I said softly.

"What's the magic word, Peggy?"

"Please may I, sir."

I don't know where the "sir" came from. He walked into the kitchen with me, and I followed him like a pet dog. He poured a drink for me and opened a beer for himself. The drink was almost all vodka, but I gulped it down; I needed to be drunk.

"Slow down. I want you awake when we use your holes."

I shuddered. I wanted to get out of there.

"While we're waiting for my guests, play with your tits as a warm-up."

I didn't question him. I cupped my boobs pushing them up as I squeezed my firm tits. I pinched my nipples, sending lightning bolts to my pussy.

"Take them out."

My knees shook as I pulled my dress open and lowered my bra.

'Bend over and shake your shoulders. I want to see them sway."

Pinching my nipples felt so good that I closed my eyes.

"His opened-handed slap to my tender boobs brought me back to reality.

My eyes opened to the sight of him getting ready to slap me again. He continued to rain blows down on my tits while laughing all the time. Tears were rolling down my face.

Finally, he stopped; my boobs had red hand marks all over them. I gently rubbed them before pulling my bra up.

"There's more to come, Peggy. Now go to the bathroom and fix your makeup; you know what I like, so don't get me angry."

With that, he held my chin and spit on my face.

"Now get moving!"

I squealed as he slapped my butt. I hurried toward the bathroom as best I could in my heels.

I tried to compose myself. Dennis walked into the bathroom without knocking.

"I brought you a drink."

I took it from him and put it on the vanity.

He glared at me. "Drink it; I want you good and drunk.

"It was a strong Screwdriver. I could barely drink it without throwing up. I finished my black eyeshadow and teased my hair as I heard the doorbell.

Dennis was thinking about Peggy and was planning to humiliate her as much as possible. The best part was waiting in the basement. She'd be sore for a month.

"Answer the door, Peggy."

I opened the door, and there were three guys; one was Phil; I knew him; I had screwed him for Dennis.

The other one introduced himself as Chris, and the third was Paul. They looked to be in their twenties.

They looked at me up and down without shame. Chris looked at my tits and just said,

"Wow, you're beautiful."

Phil reached out and palmed my tits.

"The best part is she'll let you do anything you want."

My head was spinning. Instead of pulling away, I put my hands on his, encouraging him to squeeze harder. Finally, Dennis spoke.

"That's enough for now. Let her get some beers."

I was burning with embarrassment. Four sets of eyes followed me as I minced into the kitchen. Straightening my dress. No matter how I tried to adjust, it was futile. If I pulled it down to hide my stocking tops, my boobs swelled out of the scoop neckline. It was a joke anyway. My dress would soon be on the floor. What was ever going to happen to me?

I knew Dennis was getting angry and would take it out on me.

Walking carefully, I carried the beers on a small tray. I carefully gave each of them a beer, bending from the waist, which ensured my dress crept up my legs, exposing my garters.

"Peggy likes to please, don't you? "Miss Peggy.? Tell us what we can do to you."

I was looking at the floor as I mumbled.

"Anything you want, I want to please you."

"Well, crawl your sorry ass over here and sit between us. I suggest if anyone wants to kiss her, you better do it now unless you want to taste cum on her breath."

Phil was sitting on the couch. Dennis slid over so I could sit between them. Phil didn't waste any time. He pulled me close to him and kissed me hard, forcing his tongue into my mouth, seeking mine.

The other guys pulled their chairs closer. While I was kissing Phil, Dennis looked at them and carefully started to pull my dress up. I felt it being pulled up, but between the drinks and my needy pussy, which was aching for a touch, I didn't care.

I knew this was why guys like to get women drunk.

Dennis had succeeded in getting my dress up to my black panties. A low moan escaped me when he ever so slightly brushed my shaved mound with his fingers.

I tried to escape Phil's arms. He was smothering me. I could hardly breathe.

I gasped

"Slow down. We've got all night. Give me a break."

The other guys laughed; he turned red and pulled me back.

"Whores don't get tired!"

I looked to Dennis, who just shrugged and said.

"Phils right."

They pulled me up and surrounded me.

"It's time for you to get fucked, "Grand Ma."

My ears burned. I tried to pull away, but in my drunken state, I fell, my dress twisted up to my waist.

I started crawling away. I don't know what I was thinking. They wouldn't let me go until they had cum in me or on me. Phil jumped up and grabbed my hair, stopping me. Finally, Dennis spoke.

"Peggy, you're going to get fucked, so stand up and take off your dress. Guys, you can use your belts on her if she takes too long."

Even in my drunken state, I panicked. The thought of them whipping me petrified me.

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I crawled over to him, wrapping my arms around his legs. Looking up at him, I further debased myself.

"Please don't let them hurt me; I'll do anything you want."

He sneered at my begging.

"Suck my cock, bitch. But first strip."

They let me stand, facing them. I reached around my back and unbuttoned my dress, letting it fall to my waist. My beautiful tits almost overflowed my skimpy bra. I had to wiggle to get my dress over my hips which got my boobs swaying. As I stepped out of my dress, Chris whistled.

"What a fucking body. I can't believe she is wearing stockings."

I dropped to my knees in front of Dennis and slowly unzipped his pants, his cock springing free. I covered it with soft kisses before guiding it into my mouth.

Swallowing as much of his cock as I could, I moaned like a bitch in heat. I looked around; they had all undressed their hard cocks, waiting their turn.

Dennis didn't have much control, and soon, he gripped my head and speeded up, shooting his load in my mouth.

He growled at me.

"Don't swallow it cunt. Spit it on your tits."

I meekly complied, letting his cum stream out of my mouth, dripping on my tender tits.

I think it was Phil who gripped my head and forced his dick into my mouth. He was bigger than Dennis, and I had to keep from gagging. My moaning was turning them on. But in truth, it wasn't fake. His relentless mouth fuck was bruising my lips. The other two couldn't hold out, telling Chris,

"Hold her still. I'm going to cum on her face."

I was so ashamed, a woman my age reduced to a cum target. I tried to pull away, but a stinging slap across my face from Dennis put me in my place.

"Don't try that again, whore!"

With utter submission, I tilted my head back to receive a load of cum.

The first spurt coated the side of my face. I was aware of a flash from a cell phone as another load hit my forehead, running down into my eyes.

They had finished for now, but twenty-year-old guys can reload fast.

My fingers were shaking, and I started to wipe my eyes.

Dennis stopped me.

"Clean your eyes, but leave the rest of our cum on you. Now I want more beer and something to eat."

I cleaned my eyes as best I could and headed to the kitchen. I brought them more beer and the subs Dennis had ordered. Gulping down a glass of whiskey, I headed back into the living room.

Dennis was sitting on the couch while the rest were in chairs. He patted the open space next to him.

"Come sit down, Peggy."

He had a cruel smile on his face. I felt like a cheap hooker, dressed in my bra, panties, and nylons, with dried cum on my face and boobs.

"Relax, why don't we watch a movie?"

The other guys were mumbling, "We don't want to watch porn; we want to fuck her."

Dennis laughed.

"Trust me, you'll like the star of the film."

He hit the remote, and the screen lit up. My heart stopped; it was my boss's office, and I was stripped down to my undies. They were squeezing my tits and spanking me, I couldn't watch anymore. I looked away, listening to my squeals, begging them to stop, and then they took turns fucking me on their desk.

The pigs were cheering my boss as he unloaded on my face and later made me beg for my clothes.

"I told you guys you'd like it. Let's play with the real thing."

He grabbed my head, pulling me to his crotch.

"My dick needs attention; why don't you see what you can do."

His friends snickered. All eyes were on me. To be truthful, I was frightened they all were drinking and looking to abuse me for their entertainment.

I reached out with my hand to stroke him. he slapped it away.

"I can do that myself; use your mouth." I

I was beyond humiliation, getting on my knees next to him and lowering my mouth to his cock. All the time, his friends were cheering him on.

Why does it have to be like this?

It brought back memories of my first year of college.

I didn't date much in high school and wasn't prepared for guys with experience.

I met Eric, who was also a freshman. He was the first guy to show me any attention. He was also a freshman but seemed to adapt to college life more than I did. I lacked self-confidence. When he asked me out on a date, I said yes without hesitation. We ended our date at my apartment. After a few beers, we ended up on the sofa. I let him squeeze my tits. It felt fantastic, but I wasn't ready for anything else. He respected me and left shortly, promising to call.

I was in love, so when he invited me to a party on Friday night, I said yes, way too fast.

I didn't know he was pledging a fraternity, and it was his job to provide some "Entertainment."

I have blotted out the details of that night.

But needless to say, I lost my virginity; I was the only girl there. There had to be at least ten guys. They literally poured whiskey into me using a funnel.

I was raped in every orifice. The night was finally over; I was tossed on the lawn covered in cum. Two girls found me and took me to my apartment.

I switched schools and didn't date again

until my late twenties.

Now I was faced with guys watching me suck Dennis's cock; it was really sad for a woman my age reduced to this.

His cock was hard in minutes; he smacked his dick against my face and then rubbed pre-cum all over my cheeks. I hated it.

I felt my panties being pulled down and fingers probing my slippery pussy. It was too rough for me to like it, but I started to moan.

"I don't want to watch you get your dick sucked. I came here to get laid."

With that, I think it was Phil who pulled my panties down and started to probe my slit with his cock.

Dennis was holding my head tightly with his cock in my mouth. I was starting to panic; I couldn't breathe.

They were all laughing as I was waving my arms wildly. He finally released me; I was coughing and gagging uncontrollably, spitting out pre-cum.

Dennis pushed me to the floor. I lay on my side crying.

"Don't cry, Peggy; there's more fun coming up.

Come on, you guys, grab her. I've got something in the basement to show you."

They picked me up like a rag doll and carried me kicking and screaming into his basement. It was a finished basement with a pool table. But in the corner, there was something covered with a sheet. They dumped me on the floor; I lay there, afraid to move.

I'm going to give her a drink; she's going to need it, as he poured straight whiskey down my throat.

Dennis pulled the cover off, and I couldn't believe my eyes. It was a Pillory, with an opening for my head and two for my wrists. I started struggling, but they were too strong. They suspended me in mid-air and inched toward the device. Dennis unlatched the clasp and swung the top part open. Maneuvering me toward the openings, once my head and wrists were in place, Dennis closed the top portion, trapping me.

Its height was adjustable. Dennis had that evil grin as he lowered it, so my body was bent in half. My face was at crotch level while my legs were straight, my heels making my butt stick out.

I was crying openly. I was pleading with these guys, humiliating myself.

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