Gambling Debt 2 free porn video

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After my wife arrived my friends then left our house. My wife Melanie then told Shawn that she did not think it was right for her to have to pleasure him because I fucked up. Shawn then told her that she was right.

Shawn then looked at me and told me that the conditions would change for future months. Shawn told me that he knew I had just been allowed to work from my home. Shawn told me that during the months that I could not pay the debt I would have to dress as a woman and service him. Shawn told me that I had to be dressed as a woman at all times in case he showed up.

Shawn then told me that he would have some special clothing left at a store for me for a the next month if I could not pay. Shawn told me that when dressed as a woman I had to have some breast forms with adhesive on so I would be more like a woman. Shawn told us he would have the breast forms at the store with the special clothing. Shawn then left our place and Melanie went to bed without talking to me. Shawn said that the clothing would have to be sexy.

The rest of the month went by without Shawn showing up. When we got to the last day of the month we knew we could not pay the $1000 because we would only have $800. My wife then told me that we had better go get some clothing for me to wear that month. Melanie helped me get clothes because I did not know what sizes. We got me some panties which were easy to get because my cock is only 1 ½ inch long when hard so it fit into panties well. We then got me some dresses and stockings. We could not get the bras because we did not know how big the breast forms were. We did not have to get a wig because my hair is shoulder length.

We had to hurry up because Melanie had to go to work. We went back home so she could go to work. I then realized that we did not go to get the items from the store he told me to go to. I called Melanie to see if she would get the stuff but she said no that I was the one that fucked up so I had to get it. I then went to the store.

When I got to the store I went to the clerk who was a very hot looking 18 year old woman. I told her what my name was and that someone had left a package for me. So she went and got the package and handed me a envelope and told me that she was to relay a message for me to open the letter when I got home and not to look in the package. So I then had to ask her about the breast forms and she told me what size they were so I could be some bras. I was so embarrassed because I had never even thought about wearing women’s clothe and here I am shopping for them. I paid for my bras and went to leave when she told me I would look good in the clothes that were in the package.

I got home and opened the envelope. The envelope said that I had to be at Shawn’s place at 6:00 PM or he would be at mine at 7 to collect the money. It went on to say that I had to be wearing the clothes in the package and have my nails and make-up done. The note also said that I had to get rid of all of my hair except what was on my head.

I then opened the package and found a the breast forms, black French maids uniform, black bra, black heels, a nametag with the name Stacy on it, black stockings, black garter belt, and black panties. The panties had SHAWN’S bitch, DECEMBER 08 wrote on the back in white. At that point a feeling of dread came over me.

Melanie came home and I told her what I had to do the next day. I had to ask her to do my nails, make-up, and hair for the day. Melanie agreed to help me.

The next day we woke up and I took and shower. I used Melanie’s hair remover all over my body. Melanie then started to do my hair make-up and nails. Melanie then left the room because she did not want to watch me get dressed. I was happy because I knew she would see what I was wearing but I did not want her to see the panties.

When I started to get dressed I noticed a letter inside the box with the clothes. It said that I had to wear the panties on top of the garter and stockings. I got dressed and put on the nametag. I started to leave and Melanie saw me leave and said that maybe he’ll only make you clean with a smirk on her face.

I got in my car and went to Shawn’s house. I arrived at 6:10 PM and knocked on the door. Shawn answered and said I was beginning to think that you were going to have my money this month. Shawn then said that I was late and would be punished. He told me to stand in the middle of the living room.

Shawn then listed some rules

You will refer to me as sir or master.
You will do what is ordered without question.
You will answer to Stacy only.


Shawn then asked if I understood the rules and I replied yes.

Shawn then told me to come to him and take off his belt. Shawn told me to go bend over the coffee table and put my hands on the table. Shawn told me that I would receive punishment and asked me if I knew why. I told him because I was late. Shawn told me that I would also receive punishment because I did not say sir or master.

Shawn then got up and gave me the hardest spanking I have ever had. Shawn then told me that I had to count the spankings out loud to him. He told me that I would receive 10 for not saying sir and 1 for every minute I was late. SMACK! 1 sir. SMACK! 2 sir and he kept going until he got to 20. I started to tear up because it hurt so bad.

Shawn then asked me if I was going to disobey anymore and I said no. Shawn told me to go get him a beer from the refrigerator while he sat and watched the game. When I brought him his beer he told me that I should make it up to him for disobeying while he was looking towards his cock. I then sank to my knees and unzipped his pants. I could not believe that I was about to suck his cock again but this time dressed as a maid. I did feel relief because it would get it out of the way and I would be able to go home.

I lowered my head and took his massive cock into my mouth and started to bob up and down on it. Shawn told me that he was going to like having me as his bitch for the month. He told me that he liked having bitches suck his big black cock. He asked me if I liked sucking his cock and I told him no sir. He told me that it didn’t matter because I still had to so I lowered my mouth back to his cock. I felt him put his hand on the back of my head. I had to suck his cock for a while because it the game went to halftime while I was sucking. I then felt him start to tense up and grasp my hair. I sped up my motion so he would hurry up and cum. He then pulled my head back and gave me a facial. He told me to put his cock back up. He then told me to get him another beer and get him a snack.

When I brought him his stuff he told me to start doing his laundry and wash the dishes. I started to feel relaxed because he already came and he just wanted me to clean up for him. As I was cleaning up the living room I felt him fondle my butt so I knew I was going to have to give him another blowjob.

He got up and told me to follow him. When we got to his bedroom he took off his clothes sat down on his bed and told me to get to work. I then went back to my knees and started sucking again. After I sucked for awhile he pulled me up and told me to lay on the bed face down. I really started worrying then because I knew where this was going and I have never had anything enter me before. While lying on the bed he positioned himself by my head and had me suck him some more. He told me that he was about to really make me his bitch. He told me that he was about to take his black cock and make my white ass his.

He then pulled my panties down and laid on top of me. He placed his cock in my ass crack and asked me if I was ready. I then said Please sir don’t please just let me suck your cock. He told me that he knew I liked sucking his cock but that it was time for me to become his. He told me to spread my cheeks which I did because I knew what would happen if I backed out of the deal. He then started to put pressure on me with his cock.

I felt it start to slid in my ass and it was hurting really bad so I started to moan. He told me he knew I would enjoy getting my manhood taken by him. He then told me to ask for him what I wanted. I then said what he wanted to hear “Please take my manhood and make me your bitch.”

He then really started to go at it and was hurting me. He pulled my up into the doggy style position and started to go hard and slow. When he did that it started to feel good and I noticed that my cock was getting hard. When I noticed I was hard I got sick at the thought of having him fuck me in the ass.

He then asked who’s bitch are you “Yours Sir” What do you want “I want you to cum” which I did because I just wanted it to be over. “Are you ready for my cum in your ass ““Yes sir.” At that point I just started to talk dirty to try and get him off quicker. “Please sir fuck me with that big black cock I need it now.” He started to pound my ass real hard and fast.

I felt him tense up and start to empty his warm cum into my ass. H e shot at least 8 strong shots off cum up my ass and I could feel it seeping out of my ass and down my crack to my balls. Shawn then pulled out of my ass and wiped his cock on my ass cheeks. He then told me to put my panties back on and meet him in the living room. When I got to the living room he told me to get into position for some spankings. He told me that I was to receive spankings before I left every time I came over. While I was bent over I could feel his cum leaking from my ass and into my panties. He told me that I was not to take the uniform off when I went home and I had to let his cum soak into my panties. He told me that I could not take the panties off for anything not even to use the restroom. He told me that I would have to hold it all night. He also told me that I could not clean off my face. He told me that I had better not cum into my panties. He told me that I could not have sex with my wife either.

Shawn told me that when I got home I had to get on webcam so he could see that I was following directions. He told me that while on webcam I would have to show Melanie the back of my panties. He told me that on the next day I could take a shower at noon. He told me that I could not wash the panties.

Shawn then told me that for the entire month I Had to leave the panties on display on my dresser with the back facing up. He told me that I would have to have them on display for any month I was in his service.

I then went back home it was about midnight. Melanie was asleep so I turned on the computer and woke her up and told her I had to show her something. Melanie then made the comment “I see he made you clean him up and you got all messy.” When Shawn got on webcam I turned around bent over and raised my skirt so she could see. Melanie then burst into laughter and told me that really was his bitch.

When Shawn got off of webcam we got into bed. Melanie then placed her hand on my cock and started to stroke it. It felt so good because she did not touch me anymore but I had to stop her because I did not want to get punished. “You really are his bitch aren’t you” she said and rolled over. "I bet you liked having his cock in your mouth and ass you fucking cocksucker" she said

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Jen and Sam had been together since junior high school and neither had been with anyone else when they married right out of school. That had been twenty years ago.From the very start of their relationship, they’d declared they didn’t want kids and Sam had even used condoms even though Jen was on the pill. A few years into the marriage, Sam had a vasectomy.Sam liked a gamble and Jen didn’t mind at first because he only bet on the occasional sports game and it wasn’t really that much money. But,...

Quickie Sex
2 years ago
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Slutty Kerry gets into debt

Slutty Kerry gets into debtKerry was just 18 when she came to work for me as an office junior. Even as a school leaver she seemed very forward and though she was a little overweight she was more than willing to wear low cut tops and short skirts to work which went down very well with the men who worked in the factory.She had a boyfriend but was more than happy to let everyone know that she was also seeing a married black man.It wasn’t long before she was cadging cigarettes from the men in the...

4 years ago
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Daddys Big Debt

In fact, she couldn't quite remember what she was doing stark naked in the middle of her dark bedroom. With a muffled groan, she tried to prop herself up on her elbows but only got as far as the groan - she was tied in place. "Oh my God!" she thought. This was a bad dream. It had to be! Desperately she tugged at the restraints on her wrists above her head. Now that she was fully awake, she could see that she was strapped down on her own mattress, completely stripped and...

2 years ago
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Daddys Big Debt

Introduction: Its my first story of this kind. I classify it as hardcore, so if youre not into this stuff, please dont read any further. If you do, I hope you enjoy. Please leave comments. =) Dahlia couldnt remember where she was. In fact, she couldnt quite remember what she was doing stark naked in the middle of her dark bedroom. With a muffled groan, she tried to prop herself up on her elbows but only got as far as the groan – she was tied in place. Oh my God! she thought. This was a bad...

2 years ago
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Paying Off a Debt

My name is Burt. I’m a big good-looking twenty-five year old guy. I know I shouldn’t have included good-looking in that description, But I’m not bragging. I didn’t have anything to do with it, so I can’t claim credit for it. It’s just the way it is. After all, people have said it to me hundreds of times over the years. I said big. I’m 6’2” and weigh 210, but I’m solid, no flab. I’ve been married a little over two years. My wife Patty is beautiful. She’s one of those petite perky types with a...

Gay Male
1 year ago
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Free from Student Debt

As I left for medical school and into student rooms, it was the first time I had share my personal space with anyone. Christy was my roommate, 20 years old, one year older than me, but more worldly wise than I. The room itself was small but with 2 beds, a small study area each, a worktop stove/oven, a microwave on the side and a small but usable bathroom. The only issue was it only had a shower, no bath and the sliding door would not slide. It was a hot day when I arrived, and on opening the...

3 years ago
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Jan pays her husbands debt

Jan was looking forward to tonight. Earlier that morning her husband Rick had given her a key card to a suite at a five star hotel and said he'd meet her there after he got off work. "Wear something sexy," he said. She definitely would. Jan was an obedient wife. Plus, she liked the idea of a spontaneous and naughty adventure. Since Jan was a housewife and well taken care of by Rick, she spent all day getting dolled up. She went to the spa to exfoliate her skin and make it nice and soft. She...

3 years ago
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Michelle Settles My Poker Debt

Michelle Settles My Poker DebtIt was one of those situations I had heard about but never believed. Three friends were over at my house playing poker, and I was down about $300. It was a string of bad luck, really. My hands had been good all night, but someone else always had something a little better. Now, I am sitting here with a ace-high flush, the other three guys have gone in, but I do not have enough money to match them."I am short, guys. Can I put in my watch? Its worth $200." "I don't...

2 years ago
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Gang Debt

Lady Clarissa had beed dragged from her mansion by the angry mob  Thursday?Jane, you need to get those reports typed, by tonight. They need to be FAXED by end of business. Mr Carter is here tomorrow to look at the closing accounts. Don?t forget Mr Barns is back Wednesday so everything has to be sorted by then.The legit accounts are sorted, no problem, but the others need some work. We don?t want any upsets or Barns will have our arses?. Miriam watched irritably at Jane messing with...

3 years ago
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GAMBLERS DEBT

She walked past me to the gaming tables and I got a second look at those brown eyes and a pretty face, before a whiff of her expensive perfume assailed my nostrils. I turned, just in time, to see her hips sway back and forth inside her tight fitting dress. The wolf (me) watched until she disappeared around a corner. Now the little head was doing the thinking, heh-heh. I wandered into the gaming room and saw her standing at the roulette wheel. Her modest pile of chips seemed to be dwindling...

1 year ago
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Wife Settles Husbands Debt

I couldn't believe that I had done it again. My wife warned me not to gamble anymore, especially with Tony and Rick. But they were the ones that would give me any action, everyone else had cut me off. This time I really messed up. I was in way over my head. There was no way I could pay this loss off, I couldn't even afford to pay the weekly juice. It was no use running because I worked with Rick and they'd always know where to find me. I met them at the bar on Friday night and tried to...

4 years ago
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Shayna Pays a Debt

I stood there on Jimmy's front porch, pounding frantically on his door. When he had called a few minutes earlier and asked me to come over quick there was a nervousness in his voice that told me that he really meant it. Something unusual was going on. I had dropped everything and run over to his place as fast as I could. Now he was making me wait in the hot sun. Finally the door opened. "Hi, Shay." No smile or hug or kiss on the cheek. Something was definitely up. "What's goin' on,...

1 year ago
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DEBT

Jacob woke up. Tired after waking up he checked his phone. He saw notification... NEW MESSAGE FROM LAURA. He hapilly opened it, but was shocked right after. It was picture of his girlfriend and her dad, chained to chair with ducktape on their mouth. There was also pinned adress down below. He couldn't understand what was happening. In the moment he got another message saying "If you want to ever see her again... in one piece... don't call police." His hearth was beating so fast, he didn't know...

1 year ago
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Anna pays his debt

Anna was laying on her couch waiting for her boyfriend Mike when she was startled by a loud knock at the front door. Thinking it was Mike she went to the door in her tiny tank top and shorts, Anna was surprised to see a large black man at the door who was looking for Mike. The mans name was Carl and it seemed that Mike owed him some money. After Anna told him Mike was not here Carl insisted he would wait and forced his way into the apartment. After a few minutes Anna notice the man glancing at...

Interracial
4 years ago
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Wife and daughter forced to pay off husbands debts

Part 2The casino was buzzing. Someone had just won big. I felt pity for whoever it was, they’d lose it again so quickly. The house always won. Won no matter what. The croupiers were all smiles, smiles and fake tans. Fake smiles. They knew, as we knew. The other punters smiled, their fake smiles, patted each other on the back. Their “why isn’t it me” fake happiness. They didn’t know, didn’t understand, that the house would win, no matter what…………….Tris, my ex-husband. My gambling addict...

1 year ago
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The Game of Debts

Ella felt the haze of the chloroform leave as she woke up in a foreign room. The walls were blank, and the single, steel clad door was missing a knob. In front of her stood a table with some clothing, neatly folded next to a large, pink dildo, standing tall with its suction cup etched to the metal of the table. Behind the table, etched into the wall, was a giant screen showing her in unflattering high definition as she woke up and crawled to her feet. In the right corner of the screen she could...

3 years ago
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Wife and daughter forced to pay off husbands debts

I lay on the lounger beside the pool. The sky was blue. The sun was hot, hot on my naked back. I was nude, of course I was. He didn’t like tan lines. I sipped my drink. Iced water, with a slice of lemon. I looked over the top of my sunglasses. My daughter lay a few metres away. She was asleep, flat on her back, her legs splayed. Her tanned skin glistened, a mixture of sweat and sun cream. I watched a bead of perspiration, as it rolled down her pussy, then disappeared between the cheeks of her...

1 year ago
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Paying off debts

Linda Kwong-Norton was full of foreboding ahead of the meeting with Wang Sze-wing. The slim 37-year-old Hongkong Chinese beauty and her American husband, Brad, owed him a lot of money after their business got into trouble. As they sat in Wang's office, she gave her husband a quick glance, raising an eyebrow ever so slightly. He gave her an almost imperceptible shrug in response. She made a weak smile and returned her nervous attention to the portly Wang seated behind the desk before them,...

Group Sex
4 years ago
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Babysitter Gets Caught Then Gets Schooled Shocking Revelations Final Lessons Collecting Debts

Introduction: When the twins walk in on a lesson session, thats when more secrets are revealed. And so both Jason & Joey give the babysitter her final lesson. As Jason and Joey both just sat there still stunned by what theyve just walked in on, Joey notices the wine bottle I bought for me and their mother for our wedding anniversary that was half empty. Then Joey begins fuming(as they both begin to put two & two together, immediately suspecting Kayleen),.., Let me take a wild stab, this is the...

4 years ago
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Gambling My Wife and Black Business Partner part 6

CJ has another plan up his sleeve as my young wife is out of it and now helpless to resist anything that can be done to her. The trip back to the Edgewater hotel is short as the Porsche comes to a halt in the parking garage level that is next to the the hotels topless bar. Several men are standing by their cars as they come to a stop.. CJ has gotten out opened her door and motioned for the men to come over, he has undone her seat belt. She is definitely out of it and has no idea where...

4 years ago
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Gambling Affair

Sitting at her kitchen table drinking her coffee as she reads the morning paper, her routine is similar each day. In fact she makes sure to do the same things every morning, she doesn’t like to be rushed. Reading one of the stories on the sports page, she jumps when her phone rings. Taking it from the counter, she answers without looking to see who it is. ‘Hello?’ ‘Keira?’ ‘Yes, good morning Adam!’ ‘Keira, I know this is last minute. But I would like to sneak away to Vegas with you for the...

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