Ok here is my dilemma ....

I have a Twin brother who recently got married, However he has this trip to Las Vegas planned for like a weekend of Gambling with his mates, I'm not going and he doesn't wan't his wife to find out. So I will be taking his place at the office, she thinks he will be staying there for the weekend.

Dilemma is do I just go along with it? or do I risk going back to his and maube getting some from my Sister in law?

Help me out.

The following is not real. Some of you know have known me will recognize some of the people, but this is not how this actually happened. People suggested I try writing something else so here you go.

So, Im going to be straight up for a second. I think about fucking everyone I meet. I think about how they would feel under my hands. Or how I could make them cum. I think about what kinky stuff they might be into. Is the fat old charge nurse into anal? What would that paramedic do if I asked him to piss on me? Would the clerk that checked me out at the store rim me if I went down on him?
All of these and more race through my mind. Normally I push them out of the way. Sometimes I dwell on them, and try to find out. And that’s how it was with my father in law.
From the moment I saw him, I wanted to fuck him. Joe and I had just started dating and we had gone to his parents house. My future father in law (lets call him Frank) was a runner. Not just recreationally. He liked to do marathons and shit like that. As such, he was in amazing shape. Athletic and slim. His muscles were well defined under his skin, and he had the sharp facial figures like a sculpture. His hair was still black, aside from the gray that had begun to appear at his temples.
To be fair, I was in shape then too. More than one, actually. They were just circles of various sizes.
From that day forward, I wanted to fuck him. I wouldn’t say I was obsessed, but I did think about it often. I was still occasionally fucking Joe’s brother, so I would find myself comparing their cocks. Joe’s wasn’t small, necessarily, but it lacked his brother’s girth. I began to wonder what it would take to get Frank to fuck around on his wife. He had raised one son to have an intense moral direction. Joe doesn’t like anything I like in the bedroom, mostly because he finds it degrading to me.
On the other hand, his other son was a complete dirtbag. He was the one that came on to me first. To be fair, I kept it going after the wedding, but he could have said no. What kind of a guy fucks his brothers wife the day they leave for their honeymoon?
So what kind of guy was Frank? One of his sons was an outlier, but which one? And then what kind of woman would not only entice him to cheat, but to fuck his sons wife as well. It was the kind of challenge I rose to. I had to find out. It would be quite the accomplishment, fucking all the men in a family. Well, aside from mine, I guess.
It would be a process. A long one. Find out if he would cheat. Find out if he would cheat with a fat girl. Find out if he would cheat with a fat daughter in law. Finally find out if he wanted a whore or an angel. I could do either, but angel was temporary. I would see him pretty regularly, once week or so, more often during the summer. He had a pool, you see, and Joe loved to swim.
So I got to work. First step was to see if he was even interested. I waited until the next time we went swimming. That would be a few weeks away, so I contented myself through masturbation that mostly involved him and my dad tag teaming me. By the time we were actually going, not even these clit sessions could tide me over.
I had thought about doing a two piece, but I couldn’t bring myself to do it. So I settled on my one piece. It would be sufficient for this. The changing room was their bedroom, and it had a sliding glass door that led to the pool. There was a curtain to pull to cover it. I thought about leaving the curtain open, but there was never a time when he was the only one in line of sight. Disappointed, I headed to the pool to join the others.
It was while swimming that I saw my first opportunity. The pool itself was a saltwater pool, and at one end was a hot tub fixture that overflowed in a waterfall into the pool itself. Frank was standing by the waterfall, talking to Joe, who was in the tub. I dove under the water, and while I swam to the waterfall, I adjusted by suit so that I had a nipple peaking out. I wasn’t able to be sure, and I didn’t want too much to show, but it was a gamble.
I rose out of the water next to Frank, my left nipple exposed. I slid up next to him and asked what they were up to. Joe couldn’t see my tits from his position, No one else would be in line of sight if I turned towards Frank. Slowly, with the waterfall falling on me, I turned towards him and asked him what he was drinking.
He looked to me and opened his mouth to answer, but his eyes went right to my tit. I held my breath. Would he say something? Would he freak out? Would he just stare?
The latter. As he responded to me, I slowly exhaled the breath I had been holding. His eyes were flicking between Joe, me, and my nipple. I was looking him over too. His chest had a small v shaped patch of graying hair, his nipples sat flush against his body. His neck was ridged by firm tendons and muscles. Fucking hell he was sooo hot. Joe began moving toward the stairs so I dipped down and fixed my suit.
I swam away eagerly awaiting my next chance. I was optimistic about this thing for the first time. Pushing the envelope and taking chances were such a turn on for me that I was spent the rest of the swim time rubbing my clit hidden by the water.
We caught eyes a few times after that, but he didn’t really betray anything else. A plan took form. I would be the last to get out. I would go into the room to change, and somehow entice him in there once I had stripped out of my suit and covered myself. Then, a quick flash, or something. I wasn’t sure yet.
As luck would have it, Frank and I were the last two. Improvising, I got out and piddled around outside until Joe had finished changing. I went in, and began to look around the room for something to give me an excuse to get him in here. I had to hurry, and act while he was alone in the pool area. If anyone else was there, they might come instead.
It didn’t take long. There was a hamper in the bathroom for towels, but Joe had been Joe and just piled them on top of it. Under the pile of wet towels, it might be missed. I stripped out of my suit, and wrapped myself in a dry towel. I rushed to the door and looked out. He was still alone, but he was out of the pool.
I slid the door open. “Hey Frank. Where do I put my towels?”
He looked at me in the towel, and flipped his head to the main doors into the house, possibly to see were everyone was, then back to me. “I-In the bathroom, Claire.” He said.
“I looked I don’t see it. Can you show me?” I asked. Deliberately I looked down. His wet trunks clung to his body. It wasn’t hard to see the outline of his cock, hanging flaccid, along his body. It was hard to gage, but he looked bigger than either of his sons. I let my eyes linger, then went back to his face. I bit my lower lip.
Wordlessly he started towards me. “Thanks, Frank.” I said, retreating back into the room before he got there. Now what? I thought to myself. Just dropping the towel would be a high risk high reward situation. If he reacts poorly, it might be impossible to say it was just an accident. Instead, I sat on his bed, facing the bathroom. I spread my legs, leaving the towel on, but parted just enough.
He came in and stopped. My breath caught again. For what seemed like an eternity he stared at me. He smiled slightly, but it was gone as quick as it came. He moved to the bathroom.
“Oh.” He said as he rounded the corner. “Fuckin’ Joe.” He said. He leaned down to begin picking the towels up. He turned his head to me. His eyes right between my legs. I know he could see my pussy. “Does he at least put thigs away at home?”
I just shook my head, looking at him. He looked away and stood. “Well, there’s the hamper. You can put the towel in there.”
I stood, bent over to grab the wet one I had used, and walked into the bathroom, passing him in the door way. I turned sideways, ass to him, as I slipped through. I stuck my ass out, and brushed it across his groin, feeling his bulge as I did so. I dropped the towel in the hamper.
I turned to Frank. He was staring at me. “Can you hand me my clothes? They are on the bed.” His face was red as he turned and proceeded into the room. As soon as his back was turned, I went for it. I dropped the towel. He returned and stopped as soon as he saw me. “Thanks.” I said. And I took the clothes. He stared at me. At my tits. My pussy.
“Claire, I-“ he began. I closed the door.
Fuck. I needed to cum. I heard the door slide open and then close. I thought about his cock, I thought about him pinning me in the doorway and forcing it into me. I wondered if he would try to fuck my ass. My fingers went to my clit. It didn’t take long before I was cumming.
After, I took stock of where I was. I had gone for broke. It hadn’t blown up in my face. And I felt like I knew he would cheat. I felt like he liked big tits, and I felt that he wanted me to be slutty. Maybe this would be easy.
I was wrong. The next few swim days he was noticeably absent. His wife had said that he was running errands or something like that. She never seemed bothered. I fucked myself after one day imaging he had told her and we were going to have a threesome.
The next chance would be an unexpected one.
It was Labor Day. I remember because I was off and Joe worked, taking the double time that he would get. Joe was already gone when I woke, and knowing that I would have 7 hours in the house alone had me wet thinking about who I was going to have over to fuck. I had begun to flip through my contacts when the phone rang, the caller ID showing it was Joes cell. My heart sank. He had to be telling me that he was coming home early.
“Hey, babe.” I answered, forcing a yawn.
“You just getting up?”
“Yeah. Whats up?”
“I need you to do me a favor. I need you to go into the garage and grab a tool and bring it to my dad.” He said.
I sat straight up. “Yeah I can do that.”
“Mom has the car and she’s out at my aunts. He told me not to worry about it, but hes been looking forward to this project for a while.”
“Sure!” I jumped out of bed as he talked me through the garage and the location of the tool. Once identified, I let him go, and began to plot my course of action.
He was clearly hesitant. But he couldn’t trust himself around me. He knew what the game was, he knew he would lose, and he was just trying not to play. I needed to be able to get him to the table.
Clothes would be key. It was a little cooler, too cool for shorts, but leggings would work. No panties. The top would be a little trickier. My tits are huge, H Cups. Braless wasn’t an option, but I had an ill fitting balconette that let the tops of my areolas pop out if I positioned it right. A white camisole and light black sweater completed the outfit. I checked myself out in the mirror. A quick tug on the camisole brought a hint of areola into view. Perfect.
I went out to the truck, threw the tool in the back and headed off to my in laws house. The whole ride over there I had the butterflies in my stomach that were my vice. That anticipation of something new and different. The pushing of boundaries, the taboo of the act, the risk of getting caught. All were combining to give me a high that nothing else could touch.
By the time I pulled into the gravel driveway, my pussy was aching. As I rolled to a stop, I realized I hadn’t even thought about what I was going to do. I had been so preoccupied thinking about fucking him, that I hadn’t even bothered to think about how I was going to do it.
As I got out of the truck, Frank came out from the side of the house. He was in jeans and a long-sleeved red shirt. Sawdust clung to it. He stopped when he say me, but then continued on.
“What are you doing here, Claire?” There was a tinge of anger. Good.
“Joe told me you needed this.” I went to the back and pulled out the saw.
“Yeah I told him not to worry about it.”
“Well he worried.” I passed the saw to him.
He looked me up and down. “Tell him thanks.” He said and then turned with the saw and headed back to the house.
Fuck. This wasn’t working. I watched as he turned around back. He was resisting, but I saw it in his eyes. I know that look. Seen it in plenty of men’s eyes. I pulled the black sweater off, threw it in the truck, and headed off in his footsteps.
I rounded the corner and saw him in his workshop. Formerly a detached garage, he had turned it into his hobby room a few years ago. There was a piece of wood on two stands that he was measuring. A few stools and chairs littered the perimeter of the shop. When he saw me, he stopped and sighed.
“What are you working on?” I asked.
“Claire, why are you here?”
“Im bored.” I said, biting my lip. “Joe is at work, and hes not as entertaining as he could be even when he is home.
“W-well I got a lot of stuff to do here, and I’m not going to be entertaining anyway.” He returned to measuring.
“Well, anything is better than being alone at the house.” I found one of the rocking chairs and sat in it. So far, so good, but I was running out of moves. The silences persisted for a few minutes while he measured and marked different pieces of wood. Then it hit me. I had a plan. All I had to do was wat for my opening.
It didn’t take long. After about 5 more minutes of silence, he left to go inside to get something. I took my shot. As soon as he was gone, I jumped up and headed for the pool. Flipping the cover on the control panel, I flipped the tub to on. I raced back to the shop, and I stripped off all my clothes, placing them in the chair I was sitting in. I then raced through the brisk air to the tub, where I slid in.
The water was ice cold. My nipples immediately hardened. The water coming from the jets was warm, but still, my teeth began to chatter. I prayed the water would heat up quickly.
I heard the side door open. He was heading back into the shop. It didn’t take long before he rounded the corner. I waved at him. He slowly walked over.
“Claire. What the hell are you doing?”
“Entertaining myself.” I said. I made a show of pushing my hands down to my pussy. “Since you wont, I have to find something to do.”
“This ain’t right, Claire. Theres something wrong with you.”
I smiled and closed my eyes as my fingers slipped inside me. “Mmmhm.” I moaned in agreement. “Very wrong.” I said.
He watched me finger myself. He didn’t leave. I went all in. I stood and began to walk out of the tub. The chill in the air brought my chattering teeth back. “I’m going to go into the house and Im going to be entertaining myself. If you are bored, you should follow me.” And I headed for the sliding door.
I entered, thought about the couch, but decided against getting it all wet, and went to the floor instead. I got down on all fours, ass in the air, and began to play with my pussy. I rubbed my asshole too.
I heard the door open and smiled. I had won.
I rolled over and lay on my back. He stood over me. He began to undo his jeans and I moved to my knees. “You are going to love this, Frank.” I told him.
I was eager to finally see this cock. As his jeans fell I reached up and took his boxers in my hands, I pulled them down.
It was wonderful. Bigger than either of his sons. A good 6 or 7 inches, if I have to guess, but thick. His balls hung in a sack covered in gray pubic hairs. I opened my mouth, and licked the length of his shaft, my eyes locked with his. From the tip to the base, and then back again. He began to grow. I took him into my mouth and began to suck. Using my mouth, suction, tongue, suction, tongue. He grew to an impressive level of fullness in my mouth. I pulled it out.
“Gag me, daddy.” I said before plunging down on it again. This time I felt him hit the back of my throat and the first gag began. I felt his hand on the back of my head as he held me there. Oh yes. He wanted a whore. I’d give him that.
He let me up and I pulled back, rubbing the slime covered cock on my face. “You are so much bigger than Joe.” I said.
“Shut the fuck up.” He said and he forced it back in my mouth. Another round of gaging began. When he let me up from it, I went back to his balls, letting the cock lay across my face. I licked and gently sucked each ball, and then I moved lower. He moved back. He looked at me confused. “What are you doing?”
Poor bastard. He’d never been rimmed. I smiled. I stood and undid his shirt. Once off I sucked and nibbled at his nipples as I walked him back to his chair. He fell down into it. I returned to my knees and the blow job. Building up a good supply of saliva, I worked down to his balls again, and then to under them.
It was clear he had been working, but it turned me on even more. Lower and further I pushed, my tongue searching for his ass. I could hear him moaning. I reached up and grabbed his cock. Mainly to keep him from jerking it and cumming too quick. I finally found it. I thought about how wanton and whoreish I was being. On my knees, with my tongue on my husbands fathers ass.
“Fucking hell, Claire.” He moaned. I pulled out.
“Betty doesn’t to that, does she?” I smiled.
He shook his head and stood up. It was his turn to take control. He turned me around and began kissing my neck and rubbing my tits. I felt his cock pressing into my back. He reached down and inserted a finger into my pussy. I felt him pushing me down and over. I resumed my position on my knees, my shoulders and head on the carpet.
“Fuck me daddy.” I said.
“Where?” he asked
“Anywhere you want.”
“Does he do anal?” I shook my head no, preparing for the possibility that I was about to take a pretty big cock in my ass. “Just my pussy.”
I felt the head at my ass. I reached back and spread for him. “Yessss, daddy.” He began to push in. I gasped when he first popped in. We had no lube, aside from my spit, and he was bigger than any I had been buttfucked with in a while. I let my cheeks go. The pain was reaching my threshold. I took my other hand and went to my clit, hoping to off set it.
That seemed to work. The searing pain became more bearable. “Im a whore. Im a whore. Im a whore.” I began to repeat to myself reminding myself that I wanted this. He began to slid in and out.
“Do you fuck Bettys ass, Frank?”
“Call me daddy.”
“Do you fuck Bettys ass, Daddy?”
“Not in a while.” It turned me on even more that Betty used to take dicks in her ass.
“Pull my hair daddy.” He obliged as he began to pick up speed. He had the stamina I expected from a runner, as well as the endurance.
He was pounding my ass now. My own fingers had brought me to the point of climax. I screamed as the cum took me, clinching my ass around his thick invading cock. I fully expected him to cum. But he slowed down. Not wanting to hurt me as my ass was clenching, he slowed, delaying his own satisfaction.
As soon as I subsided, we resumed the fucking. His relentless assault on my body. I couldn’t wait to have him fucking my pussy like this. “Im gonna cum, Claire.” He exclaimed.
“Do it daddy. Cum inside me.”
With a shudder he did. With each pump he moaned and shook. I couldn’t feel him cumming, but I knew it was a lot. I only felt it as he fell out of my ass. He fell next to me, catching his breath. I moved to my side and snuggled up next to him. “Good?” he asked me.
“Better than both your sons.” I smiled.
He looked at me shocked for a moment. Before he began to smile, letting his head fall back to the floor. “Wow. You are a whore. But you are an amazing fuck.”
I smiled and looked down at his cock. The cum coated it, but it didnt look bad. I leaned over and took it into my mouth. He looked at me with a mixture of lust and confusion. I felt his cock twitch a little in my mouth.
I pulled off it. “I want you to fuck my pussy next.”

Off topic just have to vent.

Dont gamble people. it is like a drug or worse. IT controlled me, im so depressed. What started as a fun night out with my girlfriend at the casino turned me into an addict. I started lyinng and sneaking up to the casino. I started spending all my savings.I started spending money i shouldnt of. I didnt drink and was sober.

Im 30, i have a clean criminal record. I kept chasing losses and tried to borrow and lie to cover up what i did. I then thought of illegal things to get money to support the habbit. I just turned into a different person, i dont know what gotten into me.

I had such a happy life, a great girlfriend and i blew it all. i dont see any point living. she left me cuz i lost everything and then some. i got nothing going for me and i am in debt up to my eyeballs

No clue how to recover, noway to get money... eating canned soup debating when to take my life.
had over 6figures, and now nothing

My wife's brother is an asshole who gambles and loses. My sister in law was never friendly but she was desperate so she asked me for a loan to keep her kid in school. She didn't want her husband to know. I said I would meet her at her house. 

So today I stalked someone for sex. I know how that sounds, but read on.

I was sitting on the bus back to my place from uni, I don't have a license you see, plus there's always a few chicks you can check out as you ride. Now we stop at a shopping centre and a few folks get on, and one of them caught my eye. She wasn't pretty by any means, she was middle aged, wearing clothes for a woman about half her age, with some reddish dye streaked through her frazzled blonde hair. She looked sort of haggard. The best way I could think of to describe it would be someone who used to be addicted to crack and has recovered, but the damage is slow in reversing. Anyway, she got on the bus and cracked open a can of bourbon and coke when she sat down near me.

Now I'm no great looker, my features are average but given my shaved head and my goatee and my rather large build, I look like a biker. Still I don't have too much trouble getting girls, some of them like that dangerous look. But anyway, it'd been a while since I'd gotten laid, and with this haggard lady, no wedding ring, drinking bourbon at 2 in the afternoon? I figured I knew where she would be heading once she got off the bus, and I could practically smell the opportunity to get some pussy.

For some reason, I don't know why, but I decided that I wanted this used up woman. Something about her, maybe the hint of good looks that she'd obviously had in the past but lost, drew me in.

So I sat on the bus and stared, the bus stopped in an area I know pretty well and she hopped off, I jumped off and followed her, forgoing the trip home. As I suspected, she made her was to a bar. I followed her in and ordered a beer and watched as she proceeded to get steadily more wasted as the afternoon dragged on.

I made my move around 5ish and offered to buy her a drink. She was flattered, some young guy paying attention to her? Which shows how shit faced she was, since I look hella intimidating even if I am in my twenties.

We get to talking, by which I mean she talks and rants at me while I pour more booze into her and listen. She tells me her name is Lyn, and she's obviously into me since she finds almost any excuse to touch me, so I lean and whisper into her ear, "I'm going to take you home and fuck you till you can't stand." Not the best line obviously, it's a gamble whether it works or not, I find chicks who are really desperate for it will go for it, and tonight luck was on my side. We leave the bar, although I buy a bottle of some whiskey for the road, and we begin walking back to her place. She lives nearby, but it takes a good twenty minutes to walk there since she's stumbling all over the place, while I continued drinking and making her drink.

We get to her house and Lyn tells me to be quiet because her kids are probably asleep. I'm not a parent, but if she has kids that go to sleep at 8pm then they must be the wussiest bunch of brats to ever walk the earth.

We creep into her room, or rather I creep, Lyn clomps, and fall onto the bed. I become like an animal, I tear off her jacket and shirt and start sucking and biting her nipples while she tells me to stop and close the door, but I don't care. I pull down her skirt and leggins and her pussy is hairy as fuck. If I wasn't so damn horny I would've walked away right then, but I don't care. I bury my mouth into and go to down on her.

She lies there moaning like crazy and keeps trying to shove my head away while telling me to close the door, finally I stand up and position her so that she can't see the door, while I can, she asks if it's closed, and I say yes. Then I unzip and pull of my pants, I'm hard as a rock and ready to go. She stares up at me all bleary eyed and asks if I have a condom, which I don't. I tell her its on and shove in. She gasps and stops asking me stupid questions and focuses on trying to thrust up at me.

I begin thrusting, hard. I'm strong, really strong. So the bed starts squeaking and making noise while I ram away in her and she starts moaning and telling me to stop being so rough but I don't care at this point. I'm so horny that I've gone mad. I keep thrusting away, shaking the bed when I hear something. I look up and in the doorway are her kids. She had a daughter about who looked about twelvish and a son who was younger. They stood there watching as this stranger was screwing their mother. It made me even hornier. I bent down, keeping my eyes on the kids and start biting their mum's nipples and sucking on her tits. They just stare at me going to town on their mother, before finally I can feel my balls a ragin'. I'd thought I was banging her hard before, but for the last two minutes I begin slamming into her so hard the bed moves around the floor, she begins crying out as she orgasms and a few moments after she finishes, I cum inside her. The kids are still standing there and even though I just came, I'm still hard as shit, still in case she sees, I stand up and walk over to the door, my cock clearly visible, the daughter couldn't take her eyes off me while the son just looked away. I smiled down at the daughter and batted my wet, slimy cock against her cheek and over her lips before closing the door. That was pretty weird for me, not into the sort of shit personally. She was very cute though.

Then I returned to the bed and grabbed Lyn and flipped her over, I pull her ass up and shove my dick in her again. I start banging her away why she starts moaning into the bed. Or maybe she's crying, it was hard to tell. I just keep fucking her. I take forever to finish this time around, it begins to make my cock hurt with how long it takes for me to come, finally I do and her butt collapses onto the bed as soon as I let go of her waist. She lies there, breathing heavily like shes run a marathon, I'm not in much better shape, but I haven't finished yet. I start jerking off trying to get hard again, but its not easy. I think about what I did to her daughter and suddenly I start to harden, once again I found that odd since I generally go for women my own age.

I walk up to my cock sleeve, who's still lying there like she's dying. I pull her ass up again and this time, I spit on her ass crack. I grab my dick and rub the spit up and down her butt. I spit two more times before my mouth feels a little too dry for more, all the while rubbing the spit against her hole. I'm not big on anal without a condom, it can lead to urinary tact infections and all sorts of shit. But tonight, I just don't care. I grab my dick and begin pushing in. She's tight. Really tight. Maybe even an anal virgin, but probably not. She begins squealing, or at least as best she can, before finally I'm in and she gives this little scream of pain before just shutting up and taking it. I begin sawing in and out of her, she's so tight it feels like the blood can't get to my dick, it actually sort of hurts, which was rough as my dick was pretty tender by that point.

Still I don't stop. I keep fucking, trying to bust a nut in this lady's ass. She starts moaning again, which makes me even hornier. I keep fucking away and she begins to grind her ass against me, the slut likes it! The first fuck had probably taken ten minutes, the second one maybe forty. The third one, I have no clue. It feels like it took hours though. I was screwing her for so long, I lost count of her orgasms after three, and still I couldn't finish. I reached around and began playing with her slightly saggy tits. About C-cups, there was enough of them for some fun. I begin pinching her nipples and tugging on them really hard while I whisper in her ear what a dirty bitch she was. How she'd probably fuck her son just to get off, and she begins crying that no, she's not like that, and I tell her of course she is, she's a filthy whore.

And still I couldn't get off. My dick hurts not, my abs ache and my back feels like I've slipped a disc. I still fuck her, but it's not nearly as fast or as hard as the earlier ones. I spit on her, I degrade her as much as possible without going into scat or pissing on her, because that shit grosses me out. Finally I wrap my hands around her neck (which wasn't easy from behind with her face down on the bed, but my hands are just big enough to make it work) and choke her a little, which makes her tighten up even more, but for some reason it gets me going a little bit. I start choking her in earnest and she starts fighting back against me, I start fucking harder, the pain in my muscles burns and my dick feels like its going to drop off, but still I fuck. I plow her and scream obscenities in her ear while choking the shit out of her and finally I cum.

I blow my load deep in her ass, and I have no idea why but it was far larger than the previous two I'd left in her pussy. It was possibly the most incredible ejaculation of my life, and it was with this used up broad whose pussy was covered in hair, and a disgusting ass and slightly saggy tits.

I pull out, and my dicks got a bit of brown on it, luckily she has a small en suite which I use to clean myself off, when I come back out she's lying there face down on the bed, not even moving beyond panting like a bitch in heat. I spit on her again and put my pants back on. I was done here. I open the door, her kids are still there, although the son had fallen asleep. The girl gave me a frightened look and I just smiled back. Then I left their home, went back to the bar, called up a mate and got a lift home.

And that's my story, anyone else ever done something like this? As in gone home with some middle aged chick who's past her hotness date and just fucked the shit out of her?

Heres my confession
My wife and I have a friend that we get together with for threesomes. We've been doing it for a couple of years and obviously been around each other naked. This night would be different.

He invited me out with a group of friends for a night of partying. We went to a local tourist gambling town. The night started with drinks at the room then some gambling, I lost. Moved on to one of the clubs private rooms, where we continued to get drunk. As the night went on we discussed getting dancers for the room or a couple hookers, there were about ten of us. Everybody was in so we left and headed to the strip club. by this time I was pretty drunk, couple of guys were trying to get some girls to come back with us and everyone else was getting dances. After about an hour or so we all decided to head back to the hotel. Once there the group split up. My friend, myself an two other guys headed up to get a drink and some "powder". This was my first time trying it so I was a little nervous about my reaction. Stayed here a couple minutes then went back down to lobby area. While down there my buddy was chatting up the local talent, and agreed to come to the room. Unfortunately we couldn't find the rest of the party, and she went on to other customers. By this time the night was a bust.

My buddy and I decided to head back to his house. Once there we had some more powder and started talking about how much we liked fuckin my wife, and trying double pussy fucking. Diring this time we were both serching for porn that we would do to my wife. Then I noticed my buddy stroking his cock in his shorts,I figured what the hell, so I started. Oddly enough we started watching the same movie from different sites. After about 15 minutes he pulls his cock out and continues stroking, so I do the same. Getting a good look at him I notice he's a little thicker than me but I'm a little longer. Now here we are sitting on his couch jerking off in front of each other. The last time we did that we were giving my wife a double facial. So there we were stroking our cock, watching porn, and obviously watching each other. The guys in the movie start covering the chick with cum. I blow my load all over my stomach, and seconds later my buddy shoots his load on his stomach. We clean up and go on talking like normal. Now I wonder if he wants to go further, or if we were both just too horny from the night we had, and if so do i tell my or just see what happens during our next threesome.

I've run up a lot of gambling debts but can't pay it back.the only way is if I let them fuck my girlfriend. They have seen her before and I have sort of said it to her but she's dead against it at the moment. I have 2 weeks to pay up or she may have to let them fuck her.

I have really screwed up my life.

I'm married to a gorgeous woman for 5 years and we both have very good jobs. "The perfect couple", or, so friends think. 

The problem....I have a gambling addiction......a very bad one. My wife knows about it and is giving out to me about it but she definitely doesn't know how deep I'm in.... hundreds of thousands, over 3 different loans from him. I've been beaten, broken bones and my life was threatened.

The last time was when I was out having a drink with my wife. They came up to me in the restroom, banged my head off the wall and sink. He gave me 1 last week to pay him. 

The following day I got a phone call from him saying that he might have a way that I could pay him back, he said, "well not you but maybe my wife could if you know what I mean". I know exactly what he meant and said, " he could forget about that because she won't be letting that happen". He suggested to me to get her drunk, and I replied that she'll have to be passed out before he'd get what he wanted. He finished the phone call telling me to meet him at his club tomorrow. That doesn't sound good for me.

I called to see him at the club and thinking the worst was about to happen, but I got a shock. He had one of his minders hand me a little bag. He said, " about our conversation last night, give her this in a drink on Saturday night and he'll be calling by at midnight for part payment. It takes about 1 hour to take full affect, have her ready. Now get out of my face."

Saturday arrives. I'm sick. I don't want to do it. I can't do this. But if I don't I'm in huge trouble, I'm a done. 

It's now 9:00, I'm really, really sick to my stomach. I tell her that I'm thinking of staying home tonight have a few drinks here instead of going out. I told her I was having a rum and coke, would she like one. She thought it was a good idea and said that she'd love one. I poured her a drink and we finished our first glass and I offered her a second. As I poured it, I just couldn't put the pill into her drink, I couldn't do it. During the second drink I noticed, it was the closest we've been for a long time. With this gambling problem, we drifted apart, we haven't been intimate in a couple of years. We did nothing but fight. But tonight she was getting close to me. She had her head on my shoulder and started to rub my thigh and even rubbing off my dick and I could see her rubbing her legs together and her body at times started to quiver. She was getting herself ready for me. It was now almost 11:00, and she asked me, could she have one more drink before bed. I went into the kitchen poured out her rum and I hesitated. This sick feeling in my stomach and a lightheaded dizziness came over me as I dropped the pill into her drink....what have I just done. The pill almost disintegrated before I had my drink poured. I brought it out to her, she took a drink from the glass and........ nothing........ nothing at all. She didn't notice. It took her about the 40 minutes to finish. Her words started to get slurred, she had trouble keeping her eyes open, the pill was taking affect. She even joked asking me what did I put into the drinks. She gets up off the couch and stumbled across the room making her way to the bathroom. It is now almost midnight I went in to the bedroom only to see my wife, sitting on the toilet unconscious. She has only her bra on and her panties are around her ankles. I lifted her to the bedroom placing her on the bed, all the time she was as limp and didn't come around. I just waited.

12:30 passed. 1:00 passes. I start to feel better thinking he was too busy or just forget when.....bang, bang, bang on the door. My heart sunk.

I answered the door and in he bursts along with his 2 minders and barks, " where is she."  I lead them to the bedroom where he lifts her eye lids and then slaps her face quite hard. He said something in Russian and the 3 of them start laughing. He checks her eyes again and after that he starts to squeeze my wife's boobs. He slaps them around for a bit and then starts to feel her pussy through her panties. He then pulls my wife's panties to one side and shoves his fingers into her pussy, fingers her for a bit and pulls them out and shows it to his minders saying something to them in his language and they start laughing again, and they start to squeeze her boobs. He takes out his phone and said to me to take off her knickers and bra and as I start, he records me. When I had them taken off I got up and started to walk to the door when he called me back. He said that it was my fault that this was happening and I have to watch.  One of his minders said something to him. Again they start laughing but I'm then told not only do I have to stay but I have to record them with my wife. They took turns with her mouth and pussy. Slapping and squeezing her boobs. I could see them turning a reddish/ purple color. Her nipples were being twisted and pulled. Her face was getting a beating from the whip of a big dick, getting her mouth forced open, getting a dick pushed back her throat. Her pussy was getting rammed by their there dicks which also got her tits bouncing everywhere. This lasted for almost a hour before the first of them shot a load of cum over her face and hair. Not long after the second minder emptied his dick all over her boobs, leaving the boss ramming his dick in her pussy, finally giving one last trust and shooting his load deep into my unconscious wife. He orders me to get a closeup of his cum dripping out from her pussy lips.

They put their clothes back on and head out twords the front door when he hands me one of the slips with the smallest amount from my gambling debt and with it gives me a bag saying they'll be back next week to get his money's worth from us. 

In the morning when my wife woke she was saying that we must have had a great time. She said, " you left your cum all over me. I'm still dripping from you", as she looks down between her legs, showing me the cum running down the inside of her leg. She also said that her breasts are really tinder.

Next Saturday came, I did the same thing to my poor wife. I used her. This time I was told to sit in my car and wait until I was called, which I did. The 2 minders went back to their car opened the door and lead some man into my house. Someone else was about to have fun with my comatose wife. I waited and waited. Eventually, almost 2 hours later, the strainer leaves my house and I get called in. The boss gives me the second slip with my owed money telling me that the biggest amount is still outstanding. He told me to keep Saturday 3 weeks from now free that myself and my wife are invited to his club, VIP guests. I told him that I don't know about that. But he said that it wasn't an offer, it's a request.

What happened that night is something I'll never forgive myself for. Me and my stupid gambling.

I'll write what happened that night, if there is any interest.

I admit that I seduced my prudish girlfriend on our first date.
I met her on a dating site and agreed to pick her up from her house. she still lives with her dad and I live with my parents as well. I took her to the nearest city with a downtown area and we walked.

It honestly wasn't that hard, I just used a few tips I had picked up from reading pick up forums a couple years back. I made her laugh, flirted lightly, and took her hand on a gamble as we crossed the street. It stuck, and we were holding hands the rest of the date. I even took her to the top of a parking structure where we made fun of people and I massaged her back and shoulders.
She is black, around 5'4 with a nice ass. she has voluptuous curves but isn't fat, has decently firm c-cup breasts and a very cute face. I'm white, 6'4 and athletic because I move furniture.

We eventually came back to my house and made a fire and started making out. I picked her up from the fire and took her up to the treehouse in the back yard and eventually had her clothes off as we made out. I didn't fuck her that night, she wouldn't let me, but I fingered her.

She's had one other boyfriend and he was the only one she slept with before meeting me. Until then she'd never been seduced.

No pics of her face, but if you ask nicely, perhaps tits.

I am the best. Just give up the thongs now in my tribute, ladies. You will never do better than me so don't even try. I have a huge 4" penis to pleasure you with and my momma tells me I'm a very handsome young man....or she did once...I think. I can't be sure - I might have been drunk. That's not true. I don't get drunk, I get awesome! Several things you don't know about me: I'm bipolar. This just means I like both poles. I'm an alcoholi.....I mean "awesome-olic". I have anger management issues but so does Charlie Sheen and he's cool, right? I'm sure your other male-friends with anger management were great to you but it didn't work out because you were so "mouthy"? Well no problem there. I rarely listen. Oh yeah I forgot, I have a gambling problem. Well....it isn't so much a problem as it is a retirement strategy.

In the last 2 yrs I've had sex with probably 650 women. I'm not bragging I have a problem a very fucked problem.

It all started after my gf and I broke up. I was 27 she was 26 and I had been ring shopping for the last 6 months. I had about $5000 saved up before that and was almost at my goal of $10000. I was going to go the next Friday when I go paid and buy an engagement ring. Thursday night before my gf called and said she was going out with some gf's and should would come by later. I said fine bc I had to work late. Anyways I was shutting everything down for the day and decided to check facebook. One of the girls she said she was going out with posted on facebook a picture of her and another of the girls at their apartment saying something about staying in for the night. I thought it sounded weird and just decided to drive by my gf's house. When I got there a truck was parked outside that looked vaguely familiar and her car was in the driveway and the lights were on inside. I had a spare key and decided to check things out. I walk in the house and don't see anything but I hear something coming from the bedroom. I go back there in look in the door and my gf is getting plowed by her boss who is probably 50. I grabbed a vase by her door and smashed it over his head. When he hit the floor I kicked him in the gut and left him laying in a pile. I walked out to my car a grabbed my putter out of my golf bag and tune up his car and leave. My gf shows up an hour later crying telling me she's sorry and that it was a mistake. I show her the money I had saved up and tell her what it was for. She starts begging me to forgive her. I left her sobbing in my kitchen floor.

I slept in my car that night and called into work the next morning and and told them I needed some time off. My boss was a close friend and I told him the problem. He let me use all my vacation time and personal days,3 weeks worth. I said thanks went and packed a bag and drove to Vegas. I live in middle America so it took 2 dsys. I got a hotel room and started drinking and gambling. I knew I would be getting a few checks direct deposited so I had a least a week of debauchery. The first night a girls starts chatting me up. After a few minutes I realize she's an escort. She tells me she can be mine for the rest of the night for $1000.I gave her $500 down and we started to party harder. I was playing craps and was starting to win small hands. Before I knew I had won $3000. I told her she was my lucky charm and decided to take my turn at roulette. I put $1000 on red and hit. Another $1000 on black that missed. I decided to try my hand at blackjack which I've played before and knew the rules. I was playing $100 dollar hand and was winning 2 out of 3 hands. I got up $500 hands. I split 2 tens then doubled down on one first hand and hit black jack then stayed on 19 on the second . The dealer was showing a 5 she flipped and had 6 underneath and I almost threw up. She hit and flipped an 2,then an Ace then a queen to bust out. I was up $5000 grand and decided it was time to fuck this hot slut. We went back to my room and fucked like rabbits. We ordered room service and just talked then started making out again for some reason I ate her out. We fucked again in the shower. Then passed out naked around 4 am. I woke up about 10 am grabbed a beer and asked her if she could go again she said yes and give me the greatest blow job. I told her I was fixing to cum and she sprayed all over her tits. She took another shower while I ate breakfast. I gave her the rest of her money plus a bit more for a tip she said thank you and kissed me goodbye.

I checked my phone and had 20 missed calls and 100 texts from my gf. I left the phone on the bed and decided to see if I was still lucky. I started playing penny slots and quickly won a few hundred bucks. I was drinking and figured I would spend all the 2 hundred until it ran out. Afte 30 mins of no luck. I hit the jackpot for $20,0000. I cashed out and went to the room took a shower and called the escort from the night before and asked her if she wanted to spend the night.We decided on a price she gave me a discount. We went to a nice restaurant came back to the hotel and got a couples massage at the spa. We made it back to the room and had sex. She told me for a couple hundred bucks a friend would join us and we could have some real fun. Her friend showed up and she was absolutely amazing. We were having fun and the next thing I know i'm doing lines of blow of the whores ass. It was incredible. All 3 of us fucked and partied and just went bananas until we passed out. I woke up the next morning and the second girl was gone. I woke up the original girl and we fucked again. Then took a shower. Anyways I'm a week into this and have banged a couple of different hookers. I hooked up with some random girls in town for bachelorette parties and I think a married woman in town for a convention. I get a call from dad that his brother passed away and I need to come home. I fly home and do all the stuff I'm supposed to do. I go to my apartment and find that my ex gf is living there just waiting for me to come home. I walk in and she runs up and starts kissing me and telling me she loves me and wants to spend the rest of our lives together. I was pretty sad about my uncle and very horny so we fucked. I had no idea what my plans were but they didn't involve her or staying with her but I decided for the next week I would use her for comfort until all this was settle. We laid my uncle to rest and went to hear the reading of the will. My uncle was a closted gay man and never had any family his "roommate" died a few years early and left my uncle a substantial amount of money that he used to retire and travel and bang young asian men. At reading we found out just how much money he did have. $10 million dollars. He left $3million to my dad. $3million to my sister and her husband and the rest to me plus his house and car. My ex gf thinks she has hit it big. I buy out my apartment lease and move into my uncles. It's nothing crazy 2200 sq ft on 5 acres with a pool which made it awesome. His car was a yr old lexus LS 460. I called my boss and told him I wasn't coming back and had heard the news and already figured I wasn't.

I found a house in vegas for $350,000 with 3 bedrooms 3 baths and pool. I set it up online too look at and bought a plane ticket to vegas. Before I left I told my ex gf I didn't love her and that I was fucking random whores the whole week I was in Vegas. But I loved the sympathy sex she gave me for the last week. She called me an asshole and left.

Heres the bad part I flew to Vegas bought the house. All I do now is spend a few weeks in vegas gambling then fly home for a bit.the longest I've stayed is a month. I have plenty of money but spend at least half of what I win on whores,coke,and booze. I go to the whore houses in Nevada all the time. I pick up escorts at the casinos nightly and have been with 4 at a time. When I come home I got to hotel bars and pick up women who just want a one night stands. I started cruising whores on back page and craigs list. Now im picking up tranny's online. My life is really out of control I'll pay these whores $50 extra just to not use a condom. I let this super hot tranny in Vegas fuck me in the ass with no condom and she came in my ass.

I was pretty happy until I was at my parents and saw an inviitation to my ex gf's wedding on the fridge. For the past week I've been laying around realizing I'm still in love with her and I never talked to her about anything that happened. I just ranaway. One of her friends told me I destroyed her when I left the first time and when I left again she was almost suicidal. I feel broken inside.