Milf Chaperone Gets Gangbanged

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All the people depicted are 18 years or older.

Milf Chaperone Gets Gang Banged

The biggest mistake I made that night was not telling anyone. I kept secret the fact that three young men forced their dicks into all my holes. Now I am paying for it.

I deserve the trouble I'm in, but I was trapped.

Now, let me start from the beginning.

My name is Carol Morris. My husband Bill and I have one son, Tom. He graduated high school two years ago and is now twenty years old and in a college situated across the country. I was always active in school activities, so I still volunteered if they needed help, even after he graduated. My husband Bill and I live a good life. He has a high-paying job, so I don't have to work.

Turning forty-five, I have kept in good shape. My legs are long and shapely, but the feature I like the most is my thirty-four- "D" cup tits. I blossomed in my mid-twenties. Men started staring at me and haven't stopped to the present day; between my dirty blonde hair and full lips, they can't stop fawning all over me while talking to my boobs. I would be lying if I said I didn't like the attention, but I do.

Since I started dating Bill, I have always been faithful. He is the only man I ever had sex with.

When we were first married, we fucked like rabbits. I wanted to get pregnant, and I soon did. I wanted to have a large family, but complications from the delivery meant I couldn't have any more children. I was devastated. Between that and raising our son, our love life suffered.

At first, he was sure sex would hurt me, but the doctors assured me we could return to normal relations. Bill is a good husband, but I wanted to try different things. "Doggy style" was my favorite. It made me feel dirty with me wagging my ass in the air, him pounding me from behind. But no, he thought it wasn't right to have sex that way.

Before we got married, I would give him head, but it made me so horny that after a couple of minutes, we both wanted to fuck. Sometimes like his birthday or when I have my period, I wanted him to cum in my mouth. When I suggested it to him, he said he respected me too much to do something like that.

I was going nuts. I needed sex, but I didn't know whom to talk to.

I swallowed my pride, wishing it was something else, and called my sister to come for lunch.

Jean was a little on the wild side. She often joked that she couldn't remember her twenties. She had been married thrice, and her current husband was very rich and in his late sixties.

After eating, we relaxed in the family room.

"So what's your problem?"

Jean never beat around the bush. I was so embarrassed, I blurted out.

"Bill doesn't want to have sex with me anymore."

Jean sat back, smiling.

"I never had trouble in that department;"

she laughed.

"My problem was I couldn't get them to stop."

I was angry with Jean for not taking me seriously.

"It's not funny, Jean; he's, my husband."

Jean sat up and leaned toward me.

"Do you think he's gay?"

"Oh, no, ... I don't know."

In leaning forward, Jean's tight skirt rode up, exposing her stocking tops. She noticed me staring.

"Yes, I wear stockings. I'm meeting my husband for drinks later, and he likes his women feminine, and believe me, I do what he likes. He's the boss in the bedroom."

"I use my body to get what I want. This guy I'm married to now will get rid of me when a new batch of women becomes available. But it's going to cost him, and I will be set for life."

You've got to remember that men want to dominate; a blow job isn't sex. It's about power. Guys want a beautiful woman on her knees, gagging on their cock. It's fun for men to degrade women. I don't know, but your Bill seems somewhat a fairy."

I couldn't believe my sister was so cynical. Her little rant didn't help me. When I walked her to the door, she turned and said,

"I can get you a good lawyer; just call me.

She paused by the door, looking at my front yard.

"If you want to see how easy men are, watch this."

My next-door neighbor was working in his yard. Jean hitched her skirt up a little and, taking long strides, reached her car; she opened her door and paused, calling to me,

"I'll give you a call, sis."

My neighbor never stopped looking at her nylon-covered legs.

She then took her time getting in her car, ensuring her skirt was up to her waist, exposing her stockings. Finally, she closed her door laughing. Maybe she was right; perhaps Bill is gay.

The more I thought about it, the more I refused to believe it. I was going to find out. Maybe Jean was correct about looking more feminine.

I made another drink and went to the computer. The selection was endless.

I chose corsets, garter belts, stockings, and four-inch black heels. I hit the purchase button; I was drunk shopping, but I was excited. The phone rang; it was Bill. He sounded genuine, saying he would be late. I masked my true feelings and said I would wait up.

Later, one of the women from the school called and asked if Bill and I would chaperone the prom next week. I said yes, hoping we could make it a romantic night.

I was glad I had ordered overnight delivery. When my stuff arrived, I went straight to our bedroom and tried my underwear on.

I drank a glass of wine and stripped down to my panties. The first corset was tight, but I finally got my boobs nestled into the skimpy lace cups. They threatened to pop out if I bent over. Next were my off-black stockings. Never having worn stockings, I had a little problem with the clasps; I couldn't believe women had to dress like this every day. I looked at my reflection in the mirror; I looked like a tramp. I guess my sister was right; men do want a whore to use. Slipping into my four-inch heels, I modeled for myself in front of the mirror. My boobs filled my corset cups to overflowing.

I imagined myself as a hooker ready to please my client. I bent over, running my hands over my boobs, squeezing them till it hurt. I fell to my knees, using both hands to stroke my wet pussy. My body shuddered as I brought myself to orgasm. Laying on the floor, in my underwear, I wished somebody would break in and fuck me silly.

I crawled into bed, tired and spent.

Jean called. I told her about Bill and me chaperoning the prom. It was being held in a lovely hotel, and she suggested I take a room for the night so we wouldn't have to worry about driving. I agreed and called the hotel to secure a suite for the night. I wouldn't tell Bill until we were there.

The night of the prom arrived. I decided to wear my corset and stockings to surprise him when we got to the room. I was a little "Buzzed" getting dressed, or I never would have worn a corset. As I hooked my stockings, I liked how they made my legs look. I felt a slight tingling in my pussy. Maybe this would get us together. I had finished applying black eye shadow and styling my hair into a French upsweep. The phone rang, it was Bill saying he would meet me there. He had something to finish up.

I was furious but didn't let him know. I told him to hurry and hung up.

I slipped into a black cocktail dress. It showed more cleavage than I wanted, but it was too late to change.

I called our ride service. My dress barely covered my knees and was super tight. Sitting in my living room waiting for my ride, I looked down at my legs. My dress had ridden up, exposing the first of the two darker bands of my stocking tops.

I heard a car horn, and wrapping a shawl over my shoulders, I hurried as best I could in my heels. The driver got out, opening the passenger door. I thought that was odd, but then I realized he wanted to look at my legs. I gripped the hem of my dress and attempted to slide onto the seat carefully. But no matter how I tried, I couldn't keep my dress down; both stocking tops were exposed, along with the garter clasps. The driver was an older man who didn't hide the fact that he was staring at my exposed nylons.

He tried to make small talk, but I cut him off with one-word answers. When we arrived at the hotel, he gave me his private number in case I needed a ride home. Knowing I would walk home in heels rather than call him, I took it and threw it away as he pulled off.

The ballroom was beautiful, much nicer than the one I attended. Inviting the members of last year's class had become a tradition, so I recognized several of the boys who had been on my son's team. They were attending nearby State College. The problem was they were all at least twenty-one and could purchase liquor, so they showed up a little drunk.

They remembered me. They all came over to say hello and ask how Tom was doing. One of my son's teammates approached me. His nickname was "Moose," and for good reason: he was huge. He grabbed me in a bear hug, mashing my boobs against his chest. I finally broke free. He was grinning, looking at me up and down.

"I still remember that white bikini you wore to that barbeque last summer."

I blushed as another guy came over. I was standing there feeling trapped.

"Excuse me, guys, I'm going to get something to drink."

Moose was quick to offer.

"I've got it, Carol, don't go anywhere. I'll be right back."

I was beginning to feel strange. They had never called me by my first name, and the look on his face when he described my bikini made me shudder.

He was back and gave me a glass of punch. I took a sip and immediately put it down. It had a strange aftertaste; maybe it was the artificial sweetener. Moose laughed, and the others joined in.

"What the matter, Carol? Too strong for you?"

Until then, I hadn't realized how many guys were surrounding me.

"She's chicken; she probably wants a soda."

My face was burning, so I picked up the glass.

"I'll show you who's chicken."

And I drank most of the bitter drink.

"Now, you boys will have to entertain yourselves. I have to do my job."

I walked around the room, wobbling a little on my new heels. I noticed a door open at the back of the room. Pushing open the door revealed a hallway that led to a storage room. I walked down the hall; it was dark and quiet. I was going to turn around when I heard voices. I froze, trying to listen to what they were saying. I opened the door to the storage area and carefully went in. I tiptoed down an aisle. They were in the next aisle. I could hear a girl's panicked voice. It was Linda, one of the girls who graduated with my son. Her voice was quavering. There were at least two guys; one was coaxing her into drinking something. They had her cornered and were pulling at her dress, with no way to escape.

"Come on, drink up. Don't be a prude."

She was crying.

"Please, no more. I feel like I'm going to pass out."

She was being forced to drink something. By moving some small boxes, I could see them. One was unzipping her dress, letting it slide down her legs. She barely noticed. They held her head and poured the drink down her throat. Realizing her dress was on the floor, she started to beg.

"Who took my dress off? Please let me go. I promise not to tell anyone. I don't want to do anything!"

"On your knees, Linda."

With some pressure on her shoulders, she fell to her knees, almost passing out, begging them to stop.

"Please don't make me do this. I'm going to puke."

I couldn't move; I should try to stop them, but I was mesmerized. They evidently had spiked her drink and were going to rape her. But I was spellbound watching the scene unfold. My hand went to my crotch, lightly touching my tender mound. I imagined myself being forced to do whatever men wanted.

She was on her knees when one of them pinched her nose shut. Her mouth opened, and he forced his dripping dick into her mouth. She beat his thighs with her fists, but they laughed at her struggles.

I was watching them force the poor girl to deep-throat them. Her face was a mixture of pre-cum tears and spit.

I was sick to my stomach, but I couldn't stop watching. The pig was plunging his dick in her mouth, and her head was lolling side to side. After a minute, he pulled out, smacking her face with his dick, then he stepped back and sprayed her face with cum. She gagged violently, crying while vainly trying to get the cum out of her eyes.

The other guy took his place. The first one said.

"I'm going to see if anyone else wants in on fucking her. She won't remember anything."

On hearing that, Linda started to scream for help. With a dick in her mouth, it was just a pitiful moan. I lingered, knowing I had to escape, when I heard male voices heading my way.

"Are you sure she won't remember anything?"

It was Moose.

"She will be conscious, and we can do anything we want. I wish we had her in our house. Most of the brothers are gone, and we could spend some time making her crawl and beg to be fucked."

Moose high-fived him and said.

"I've got that MILF Carol Morris in my sights. I've got a couple of drinks in her, and we should be able to take her somewhere and fuck the crap out of her. These old married cunts want to get laid. Then we can send her home to her husband with all her holes filled with cum."

My heart started to pound; they were talking about me—the thought of being forced to have sex with my son's friends made me sick.

I took off my heels and crouched as low as possible in my tight dress. As I made my way out, I could hear Linda begging them not to fuck her ass, then a muffled scream and guys laughing. The sounds of her crying as they assaulted her body haunted me and, at the same time, turned me on.

I made it back to the ballroom without being seen.

I found a bottle of unopened water and sat down, still feeling woozy after witnessing that poor girl being abused. I'm ashamed of myself for not trying to stop it, but why was I so turned on watching them rape Linda, and why were my panties wet?

Bill had called, saying he was too tired to make it and was going to finish a report he was working on. I didn't bother telling him about the room, so I canceled it in a fit of temper. I would come to regret my rash decision.

I was pissed; I had a night of sex planned. I was even going to let him fuck my ass, not that he would. I just wanted to please him. But now, my only thought was to avoid Moose and his friends.

I left the ballroom and went to the hotel bar. My dress looked perfect standing still, but it would ride up when I walked.

When I reached the bar, I had to tug it into place. I had a difficult time climbing onto the bar stool. When I finally got on the stool between my tight dress and my heels, most of my legs were exposed. Two middle-aged men were sitting at a table with an open chair. I downed a screwdriver for some liquid courage.

I walked over feeling good about myself.

"Mind if I sit, gentleman"?

"It would make our night. My name is Jim, and this is Donald."

He smiled,

"I hope I'm not out of line, but you have perfect legs; your husband is one lucky guy."

I blushed furiously; I waited until they were watching and purposely tugged my skirt higher, exposing my stocking tops.

"He doesn't notice me anymore."

Donald leaned forward, touching my thigh close to my stocking top.

"He's a damn fool. You don't see women wearing stockings anymore. You should be treated like a queen."

I should have stopped him, but I didn't. He inched his hand higher. We were secluded enough that no one could see us. Reaching my garter strap, he was dangerously close to my sensitive mound.

"I think you better stop; that's far enough."

As I took his hand off my leg, he lunged forward, touching my wet panties. I visibly shuddered. He looked at Jim and winked. I acted angry but left my dress up, exposing my nylons.

They ordered me another drink, which I drank quickly. I was flirting with single men, and it felt good to be desired.

They were in town for a convention and were looking for some fun. The longer we talked, the more I realized they wanted sex. I was mad at Bill, but not enough to cheat on him.

They bought me another drink; it was plain to see they wanted me drunk. I sipped it carefully; the room was starting to spin. Looking down at my dress, it was almost to my panties. My garter straps exposed. They had stopped being nice, and I knew they wanted to get me to their room. I just wanted to go home.

There was music playing softly.

"Before you go, just one dance."

It was a command, not an offer. He took my hand. I slowly got up; I got a tingling in my pussy. I can't remember the last time Bill danced with me.

Jim pulled me close to him, my boobs rubbing his chest. I didn't object. He was a good dancer. We were dancing slowly, his leg gently forcing mine apart; I could feel his rock-hard dick against my leg. At the same time, he cupped my boob and squeezed it softly. The music stopped, but I still held him close. What was I doing? He leaned in, brushing my neck with his lips.

"Donald and I have a suite upstairs. Let's go up and finish our dance?"

I shouldn't have been surprised with the offer, with the way I acted, but I wasn't a whore. But I still acted shocked.

"NO...I'm married! Now let me go."

I pushed him away, stumbling on my heels. I grabbed my purse and headed toward the main lobby. Once there, I went to the ladies' room and fixed my hair. I looked at myself in the mirror. I didn't think I had gone so heavy with my black eyeshadow. That's what happens when you put your makeup on while drinking. The black satin choker set my slender neck off. With my hair in a French upsweep, I certainly looked the part of an "Easy lay."

I got through to the car service, but because it was busy with a convention, it would take at least forty-five minutes.

I wandered into the ballroom, and everyone was gone. I walked outside to wake up. My feet were killing me. I didn't see anyone. Maybe they had left, and I was feeling good. I had outsmarted Moose and his friends.

I turned to walk back to the lobby when a car pulled up beside me. The door swung open, and Moose grabbed me and pushed me into the back seat.

I hit my head on the door frame, almost knocking me out. Moose jumped beside me and started pawing at my dress, which had ridden to my waist. Two guys were in the front seat; one I recognized as one of my son's friends, Jeff. I didn't know the driver. I tried my best but couldn't pull my dress down; my stocking tops and garters were exposed. Moose pulled the top of my dress down, revealing my overflowing cups. He took one look at my underwear.

"I told you the uptight broads always have whore underwear on."

Jeff climbed over the seat, pinning me between them. He started playing with my tits.

"This is gonna be fun."

I was struggling with all my strength, but to no avail.

Moose wasted no time. He pulled his pants down and grabbed me, and forced my face down to his smelly cock. I twisted away, but he held me tight.

"I think she needs more to drink; give me that bottle."

Jeff passed a bottle to him.

"Now, hold her still."

I was panicking. Jeff held my head while Moose forced the bottle into my mouth; I gagged as the burning liquor hit my throat. I couldn't help myself; I had no choice as I swallowed. Between coughs, I pleaded with them.

"Please stop; I'll do anything you want, just don't make me drink anymore."

"Take that fucking dress off and start sucking."

Trembling, I worked to get my dress off without ripping it. They pulled me onto the seat forcing my face on Jeff's dick. Since I had no experience with anyone besides my husband, it was hard to judge, but it was definitely longer but skinnier.

Moose was trying to work his finger into my pussy. I tried to brush his hand away, but he laughed as he forced two fingers into my dry cunt. Causing me to scream out in pain.

I was doing my best to make Jeff cum, when I was aware the car had stopped, and I heard a door open. Then, the trunk lid. I heard Moose say.