Frustrated Milf Ch. 07

I lay on my bed for what seemed like hours. But in reality, it was less than one. I painfully stood up. I was sore all over; my nipples were screaming from the clamps. I had never experienced such pain.

Touching them carefully, I wasn't surprised to see them bruised. They were sore to my touch.

A hot shower made me feel human again. I couldn't feel too good, wondering what was next.

I gave in so easily; why would he quit? He was a control freak, and I was a submissive toy.

I guess I've always been this way. My husband was a controlling man, mostly about money. In the bedroom, he was pretty much vanilla. Never going down on me and said if I wanted his dick in my mouth, he would never kiss me again. I did a lot of fantasizing, mostly about being forced to please men.

My body always attracted men. After my divorce, I started dressing in a way my husband would never have approved of. Short tight dresses and skirts, knit tops that did little to conceal my jiggling boobs, but where I really went over the top was my underwear.

Garter belts and waist cinchers were my favorites. With online shopping, it was always possible to get what I wanted. Wearing stockings turned me on; besides their look and feel, there was always the danger of showing stocking tops. And the fact men were always trying to catch a glimpse of them.

I know now that's what first attracted Richard and led to that fateful night in his office. That's what started this mess I couldn't get out of.

Dennis did not call me all weekend, which surprised me but didn't disappoint me.

I looked over my clothes, wondering what to wear on Monday. Before Dennis monitored me, I could get away with trousers occasionally, but that was over.

Monday morning was here before I knew it. I chose a black nylon dress that buttoned up the front and shiny suntan stockings that made my legs look longer. And a new pair of four-inch heels, which was a mistake. I should have worn them around the house, breaking them in. The fit was tight and was causing me to take little steps. That got my boobs bouncing. I got a few whistles walking into the office; I acted annoyed but secretly loved male attention.

I was busy, which was good; it kept my mind off cum dripping cocks.

I hoped to get away with not having to speak with Dennis. But at a quarter to twelve, he called.

"I like that dress you have on. I don't think I've seen it before; why don't you unbutton a few from the bottom."

My dress was short when standing, but as soon as I sat down, it rode up my thighs, the first of the two darker bands of my stocking tops showing. And now, he wanted to expose more of my legs. Thank God nobody was around. I stood up and unbuttoned the first three buttons.

"OK, now turn around slowly; that's very good, Peggy. You may sit down now, but don't cross your legs."

My face was burning. I looked down at my dress and how it gaped open, exposing my nylons.

"Do you have plans for lunch, Peggy?"

He sounded menacing, and to be truthful, I was scared of him. and what he could do.

"If you do, cancel them and meet me in the lunchroom."

I was so embarrassed; this dress was revealing normally, but now, with the buttons open, my legs were on full display.

I checked my makeup and headed to the lunchroom. I had to walk carefully, reaching down to hold my dress together every few steps, drawing more attention to my legs. The lunch area was small, with just five tables that sat four. Most of the office workers went out or ate at their desks. Only the older men or the I.T. nerds ate in the lunchroom.

Dennis was already there, and I saw him watching me, delighting in my discomfort.

"That shade of nylons you have on is very becoming. I want you to sit sideways with your legs on display. And don't give me any grief, or I'll "Accidentally" pull your dress off."

I had every reason to believe he would do it.

My dignity was gone; I sat down quickly, crossing my legs and dropping my hand to my lap, vainly trying to hold my dress together. Immediately, two of the losers moved their chairs for a better view of my stockings and heels.

I tried to focus on Dennis and ignore the creeps staring at me. He was enjoying himself and said.

"We must do this more often. Maybe you could wear that white dress I bought you."

My head started hurting. He knew that dress was like tee shirt material, practically see-through. Just then, his phone went off, and he looked pissed off. There was some kind of problem, and he had to go.

"I have to go, but I want you to stay and remember I can always see you. Now get something to eat."

He left, and as I got up, all eyes were on me. I got a sandwich and a drink. I walked back to my table, flashing my stocking tops, my hands occupied with my tray so I couldn't hold my dress together. I sat down, noticing that a couple of men had switched their seats next to my table so they could get a better view. I was so dejected I felt like a tramp. I didn't dare encourage any of these lechers, so I kept my eyes looking down. Until I heard the distinctive click of high heels and looked up. I had never seen her before. She looked my way and smiled. She was a beautiful girl probably fresh out of junior college. I returned the smile and gestured for her to sit down.

'Hi, I'm Ashley; thank you for the seat. I really didn't want to sit with men I don't know."

As she sat down, she glanced at my legs but said nothing. Ashley was twenty-one, and this was her second day in the billing office. She was stunning, with blonde hair, an innocent face, long legs, and an ample chest. We hit it off instantly; she had many questions about the company. We talked freely. It was nice having someone to talk with; that wasn't trying to fuck you. Meanwhile, the men in the room were enjoying the leg show. She had on a blue mini-skirt with sheer blue pantyhose. And a tight white sweater. She laughed about the men and the big deal they made about women's legs and nylons.

"They're like teenagers when it comes to looking up our skirts." She laughed.

"I'll never understand them."

She was an innocent young woman she had no idea what lie ahead of her.

Lunch ended, and we walked together back to our offices. She said, "Maybe we could have a drink some night."

I had quite a bit of work to do when Dennis called. Of course, he wanted to know what we talked about. He told me to get friendly with her.

"Why would I do that? I'm twice her age. We have nothing in common."

"She looks like the kind of girl we could have a threesome with. I can see you with your tongue up her snatch, licking her juices. And me cumming on both your faces as you swap spit."

I was simultaneously turned on and sickened at the thought of submitting that naive girl to sicko Dennis. It would scar her for life. But I still could picture her tied up, unable to move. Her legs spread wide, my mouth on her pussy with Dennis fucking me in the ass.

I had to get back to work. I could feel myself getting wet.

The end of my day came quickly, and I waited until most people left. The parking lot was almost empty. I knew better than to button my dress, not knowing where the cameras were. I slowly minced my way to my car. If all the buttons were fastened, it would be all right. But with every step, my stocking tops were displayed with the sun glinting on my garter clasps.

I prayed no one would see me.

But of course, Dennis was standing by my car. Thank God he had his mother's car. But he had that evil grin on his face.

"Come on, nobody is around; stop fooling with your dress and let it go."

I knew better than to argue with the bastard. I let my skirt go, and immediately, the dress flapped open, exposing my legs almost to my panties. I took longer strides. My four-inch heels and the uneven ground were the only thing holding me back. When I got to my car, I was humiliated and demoralized, having to walk across the parking lot, exposing myself like a hooker.

"I wonder if you could do me a favor? A friend of mine needs a ride home. I would do it, but my mother needs her car back."

"Sure, no problem; where is he."

As I turned to get in my car, Dennis touched my arm.

"Wait till he gets here. I want him to see you get in."

My face burned, but I was scared and didn't dare refuse him. I knew that he was capable of anything.

I took a chance and asked him if I could fasten the buttons. My dress was still short, and his friend would get a good look at my legs.

He glared at me. I immediately regretted asking him, afraid of what he might do.

He gave me a sly look.

"I'll make you a deal: you can button up your dress, but you'll have to give him a hand job. I owe him money, and that would settle it. Or you can leave your dress the way it is and play with yourself till you cum while he watches you."

My mouth went dry. How was this ever going to stop him from treating me like a hooker? I looked down at my feet, unable to meet his gaze. I barely whispered.

"I'll give him a hand job."

We waited a couple of minutes in silence. I spotted Dennis's friend coming across the lot; he looked like every geeky computer nerd. Skinny, no more than twenty-one, and as God is my judge, he had a pocket protector. I couldn't believe I had agreed to this.

Dennis took him aside, and they talked together out of earshot. Finally, Dennis introduced Phil to me. He was so excited that he could barely stand still.

Dennis introduced him to me, saying.

"Phil, this is Peggy. She is a little older than us. But she still likes to have fun. Why don't you get in the car, Peggy, so you and Phil can get better acquainted."

My self-esteem was at an all-time low. I carefully sat down on the seat, and keeping my legs together, I swung them in. I was proud of myself that I got in without hiking my dress up. I looked up at them. Dennis was frowning; I immediately got a knot in my stomach.

I didn't have long to wait to find out what was wrong. Dennis put his hand on my shoulder, squeezing hard, and said.

"Why don't you get out, and when you do, give us a little leg show."

I looked up at him pleadingly; my lips were quivering. There was no sympathy in his cold eyes. I got out, and my dress inched its way up, exposing the beginnings of the first of the two darker bands of my stocking tops.

"That's better now; get back in so you two love birds can get going."

They both stood beside me. I knew what he wanted. I bent over, stretching my right leg in, and sat down, my left leg still on the pavement. In the process, my dress had ridden past my garter clasps.

"Hold it, I want a picture of this."

Dennis said, even though he had recorded everything. I was numb, sitting in my car with my dress pulled high enough that you could see my panties.

The sun was glimmering on my stockings. I felt very vulnerable.

"See, I told you she would do anything," Dennis smirked.

Phil sat on the passenger seat as Dennis closed my door. I didn't dare pull my dress down. He started to give me directions to his apartment. I interrupted him, saying, "I thought we could do this in the car."

"No, Dennis said anywhere I want, and I want my apartment."

He was a little more domineering than I felt comfortable with, considering I just met him.

"Ok, calm down. I want to know, is there anyone else there?"

"No, my mother owns it and won't let anyone live there."

Oh great, another weird momma's boy.

He didn't take his eyes off my legs the entire drive.

It wasn't too far. And when we got there, he made a point to run around and open my door, getting a full view of my legs. Once inside, he asked me if I wanted a drink. All he had was white wine. I dislike wine, but I needed something to get through this. He went to the kitchen and returned with two glasses. It tasted funny, but maybe it was supposed to.

We sat on the couch. He was so excited I was sure this wouldn't take long. He blurted out.

"Dennis said you would take your dress off." I guess it was possible, but I wouldn't call him, and risk being punished later.

I stood up and unbuttoned my dress, slipping it off my shoulders and stepping out of it. I had worn my favorite corset; it fit me perfectly except for my boobs, which were just about out of the cups. I slowly turned around, pulling my stockings tight, making sure the tops were fully expanded.

I finished my wine, and it seemed to be hitting me hard. Maybe I just wasn't used to it.

Phil took off his pants, and when he pulled his Jockeys down, his dick sprang out; it was average in length but fatter than most with thick veins. My mouth was starting to water. It was a shame this was just a hand job, but I could still dream.

I stood before him, struggling to get my boobs covered in the lace cups. I walked to him, making sure to shake my ass. I reached out and gently ran my hands up and down his shaft, forcing out pre-cum. I looked down at his glistening cock. And ran my tongue over my lips.

I was right; after about two minutes, he put his head back and moaned. His dick started spewing out what seemed like a pint of cum, covering his stomach. I kept milking the last drops out; my hand was a mess. I made sure to make a show out of licking it off and swallowing it.

He asked me if I wanted another glass of wine, to which I said yes. I couldn't leave. I had been there maybe half an hour at the most. Maybe he could go again. That's the plus for young guys. They recover quickly.

I drank my wine slowly. Whatever the reason, the wine was so good that I didn't care. I was getting drunk; I had just wanted to get a buzz on to make reality fade a little. My head was spinning after one drink. I never found out that he had put something in my drink that Dennis had given him.

He cleaned himself up and sat next to me. I hadn't put my dress on yet; I was seeing if he could get it up again. I could tell he was confused that I was still in my underwear. He couldn't look me in the eye; he was so embarrassed. So I broke the ice.

"Did you enjoy yourself?"

"Sure, it was great. Can I help you with your dress?"

I whispered, "Don't you want me to stay awhile?"

I was slurring my words, and he thought I was high.

He didn't hesitate a second. "Of course I do."

My head lolled back I was starting to feel woozy.

He took it to mean he could do what he wanted. He lunged at mean, pulling the top of my corset down and attacking my boobs.

"Slow down, Romeo, give me a chance!"

He was flustered. "I thought you wanted to do it?"

"Maybe I do, but slow down."

My mouth felt like cotton. I looked at him; he was practically drooling. He wasn't going to stop.

He had to be a virgin, but I didn't want to get hurt; he had a wild look on his face. And his dick was standing straight out. He pushed me back on the couch, straddling me, roughly pulling my panties off.

"Get off of me; I don't want this! I'm too drunk." I yelled.

He was practically sitting on me. I could barely move. He reached down and squeezed my boobs so hard I cried out in pain. He was on top of me, pinching and biting my poor nipples till I moaned for him to stop.

I tried bargaining with him, but he didn't seem to hear me.

"I'll blow you, and you can cum on my face or cum in my mouth, and I'll swallow."

"Dennis was right. You're a real whore; now get on your knees, BITCH."

My face was burning with shame. He let me up, and I quickly rolled on the floor, kneeling before him. I was so ashamed; I'm a woman twice his age begging to be abused, offering my mouth. He towered over me, striking my face with his cock. I was babbling incoherently, trying to get his cock in my mouth.

He pulled my head back and sneered at me, "Suck my dick, Peggy."

I held his dick and feverishly licked it up and down, finally putting the head in my hot mouth. At the same time, I plunged two fingers into my dripping snatch. I was tormenting my swollen clit getting close to an orgasm.

Phil held my head, still jabbing his cock down my throat. He groaned and shot his cum into my gaping mouth while I convulsed with a wild orgasm. He pulled his spewing cock out of my mouth and finished on my face. I collapsed on the floor, my hands still in my cunt.

I could hear him in the kitchen. I cleaned myself up with some tissues. I finally got my tits back in their cups and straightened my stockings. My dress was a pain in the ass with all the buttons. I heard his phone ring and heard him talking; he sounded mad and ended the call without saying goodbye.

He walked back in and said.

"You better go; that was Dennis, and he is pissed at you for doing more than a hand job.''

I sobered up quickly; I never should have driven in my condition; thankfully, it wasn't that far. I was in trouble. I drove home, hoping Phil was exaggerating. I turned down my street, half expecting to see Dennis there, but was relieved when he wasn't.

I had a rotten night's sleep, my head pounding from that wine. I got up at eight; I was going to be late for sure. Wishing, in a way, he would call and get it over with.

Dennis left me a text message thanking me for taking care of Phil, and beyond that, I didn't speak with him all week. I knew it was the calm before the storm, and I was scared.

Thursday morning, he called, telling me he would be over Friday night, and he was bringing a friend. Adding for me to dress up more than I normally do.

I couldn't stand it and asked.

"Do I know who it is?"

"Just an old friend. I'll be over at seven o'clock."

That was it; he hung up without saying goodbye.

After work, I bought a sleeveless, form-fitting dark blue dress with opera-length gloves.

I called out sick on Friday. I couldn't focus on work, not knowing what would happen that night. I was under his control, afraid to say anything.

I started dressing at six. My dress was low cut, so I chose a black lace shelf bra that left my tits supported from below, with my nipples almost showing.

A black satin waist cincher nipped in my waist while pulling my off-black stockings high on my legs; I was a mix of dread and the need to get laid.

I was going all out with dark eye shadow and fake eyelashes. I wiggled into my dress and downed a whiskey sour. I considered going without panties but decided on a black thong that covered my bald pussy. While putting my hair up, I slipped on a lace choker; all I could think about was that it would please Dennis.

My dress was a thin material that clung to my curves and ended mid-thigh. My four-inch heels highlighted my calves while pushing my butt out. Completing the look I wanted. I sat at the kitchen table, lost in thought, questioning myself about doing this, when I heard my front door open.

"Dennis, is that you?" I got up, tugged my dress down, and met him. He was alone. I was a mix of relief and disappointment.

"He will be here shortly. But first, I want to hear what happened with Phil."

He was standing close to me. He could see I was trembling.

"I had too much to drink and got carried away. I'm sorry, Dennis, it won't happen again."

"You can see this made me look like my girlfriend is a whore. You'll have to be punished."

I started babbling, "Please don't do this to me; I'll be good; please don't hurt me."

I was making a fool of myself by begging him not to discipline me, while the thought of it turned me on. I prayed he wouldn't touch my dripping cunt. I probably would explode if he did.

"Calm down, Peggy. You'll survive. I will let my friend use you, and when he and I are done with you, you'll never act like a whore again."

"Now I was really scared; who was this friend? What if he couldn't control himself and seriously hurt me."

I couldn't even run out the door; I was home.

Dennis said abruptly, "We are going for a ride." I knew it was senseless to ask where. The ride was made in silence.