Midlife Crisis and a Wife's Desperate Plea for Financial Relief: A Scandalous Proposition

My name is Dan. I'm an average 45yo white male in pretty good shape for my age. I'm a freelance computer programmer. I'm married to Jill, a beautiful woman with a great body and long naturally blond hair. She is a couple years younger than me. We have been married for 19 years. We have one son and he is off in college. She is very sexual and as many hundreds of times we have fucked over the years, we could have a had a bunch more kids but we didn't want to so she had her tubes tied and I had a vasectomy. She would not make it as a Playboy centerfold but for her age she still has a nice figure with high, firm C-cup boobs and even after all these years she still is pretty tight between the legs.

We live in Sacramento, California. Times are tight for us right now with the economy being so weak. For years I made really good money and we lived like it would never end. I usually work contract work that lasts from a month to six at a time. The jobs have always been close enough to home that I could stay in my own bed, but now I have not been able to find any work for several months. We have spent all of our savings and it looks like we are in danger of loosing our house to foreclosure. So I have come to San Francisco for a week to see if I can get any contracts here. I am staying in a cheap hotel and going out looking for work during the days.

I have been in SF for four days and that night I went to a bar not far from the hotel to drown my sorrows, so to speak. As I sat at the bar with a rum and coke, I started chatting with the guy sitting next to me. It started as just general small talk but after several minutes and my second rum and coke, he casually shifted the talk toward sex. I was starting to feel loose as I was not a heavy drinker so I went along with the direction of the conversation. I told him that I had been here for four days and was really missing having my wife to sleep with. I also told him about our money troubles.

His name was George. He was in his mid thirties and he said that his wife was in her mid twenties. While we were about half way thru our third drinks, George told me that he and his wife really enjoyed it when she sucked his cock while another guy fucked her. He asked me if Jill and I ever had sex with other people. I told him that she was quite sexually active while we were in college and after we were married, we had swapped partners with other couples a few times, but not often. I showed him a picture of her. I told him that I shouldn't be talking like this as it was making me really horny and feel bad about not being home with her.

George picked up his cell phone and made a call. "Hi Honey. I'm here at the bar talking to Dan. He's a really nice guy but he has a bad case of blue balls from not being with his wife for several days. Are you in the mood for some fun tonight? I bet it would really help Dan feel better. ------ That's great. We'll be there in a little while. Why don't you give that sweet pussy of yours a nice shave while you are waiting for us." George told me that his wife was really excited about him bringing me back to their hotel and filling her cunt with a big load of my cum while he shot his load down her throat. I couldn't believe what I was hearing but I was not going to pass up the chance. We finished our drinks and walked out of the bar.

Their hotel was about three blocks away and while we walked I asked him if this was for real. He assured me that it was. We rode the elevator up to their fourth floor room. George put his key card in the door and opened it. He held the door open for me and I walked in. Right in front of us was the bed. On the bed was a beautiful young and totally naked redhead. She had a small waist and C-cup tits with big and hard nipples. She spread her legs and reached one hand between them, using her fingers to spread her labia showing her already wet fuck hole. She smiled and said, "I was wondering if you would find someone that would like to join us while we were here Darling." George said, "Vicky, this is Dan. Dan, this is Vicky." Vicky replied. "Ok guys, let's see who can get out of those clothes first." We both started to strip. While we did, Vicky started rubbing her clit and moaning.

When I was out of my clothes, Vicky looked at my half hard prick and said, "Come over here Dan, I want to see how big that nice cock of yours gets." I stood at the side of the bed as she scooted over and took hold of my manhood. She promptly her lips were around it and it started to grow to its full firm hardness. Vicky pulled back and looked. "About seven inches and nice and thick. I'm going to like that inside of me. Would you care to taste the nice tight pussy that you are going to get to fuck?" She rolled on her back and I dove, headfirst between her wide spread legs and started licking like a mad man." Vicky lifted her hips and pressed her mound tightly against my face. George had been standing there stroking his shaft. He was about the same size as me but I could see that his equipment was not as thick as mine. He climbed onto the bed and brought his cock to his wife's mouth. She quickly started bobbing up and down on his meat. He put his hands behind her head and fed her even more of it. I could hear her making slurping sounds as he fucked her face.



Vicky pushed George away, looked down at me and said, "That's really good but I want you to fuck me now. Fuck me hard and fast. That's how I like it. Really slam it in me. I hope you can last a long time and make me cum really good." Vicky got on her hands and knees. George was on his back, under her in the sixty-nine position. "George like to watch cocks going in and out of my cunt and this gives me the right angle so I can take him all the way into my throat. My pussy is all wet and ready for you, Dan. Fuck me good."



I got on my knees behind her and between her legs. I guided my prick to her fuck hole and pushed it in with one thrust. She was tight, never having any kids and still being in her mid twenties, but she was wet and ready so I had no trouble burying myself balls deep in her cunt. "Pound it, Dan. Pound it good and hard." I did just as she asked. As I watched her take George back into her mouth I could see that after a couple tries, she was able to take his full length into her throat. She bobbed up and down and he thrusted his hips up in matching time.



I held her hips and slammed into her for all that I was worth. She was moaning around George's prick and he joined her in the noise department. "Oh fuck, I'm cumming," yelled George. As he shot his load into his wife's mouth, she bit down on his shaft and swallowed over and over. She pulled off of him and his deflating prick fell down onto his stomach. Now she worked harder at pushing back onto my cock as I pounded into her cunt. She froze and shook and yelled out in pleasure as she had a hard orgasm. I could feel her juices flooding her cunt around my shaft. I pounded her thru two more hard orgasms over the next ten minutes and finally reached the point of no return.

With a tight grip on Vicky's hips I held myself full depth in her and unloaded torrents of cum into her waiting cavity. I stayed in her till my prick stopped pumping. "Come to my mouth now. Let me suck our juices off that wonderful cock of yours." As I pulled out and moved to her front, I could see her drop her crotch down onto her husband's face and him start licking her sloppy slit for all he was worth. She cleaned all of both her and my cum from my cock and balls and pubic hair. I lay back and watched as George eat her out till she had another orgasm and flushed everything inside of her into his mouth and over his face.



George went over to a chair while Vicky started gently sucking me again. "I'm going to get you up again, Stud. Then I'm going to ride you like a cowgirl on a bucking bronco." This went on for several minutes. While Vicky was working on getting me hard again, George started telling me about something that he said would help me out of my money troubles.


"I've got a friend that makes fuck flicks. He makes a lot of money from his films. He has been looking for an attractive older woman to make a MILF film. He wants a gangbang with several young guys fucking and being sucked by this good-looking middle-aged woman. From her picture I can see that your wife is attractive and you said that you have done some swinging. Do you think she would be willing to make a film like that? Depending on how good it turned out and how long it is, he would probably pay you between six and eight thousand for it. Do you want to see if she would be interested?"



Hearing about this and Vicky's sexy sucking had gotten me hard again and just like she said, she mounted me and rode me like a wild woman. This time I lasted even longer than the first time. Vicky had two orgasms before making me cum. Again she sucked me totally clean and then gave me a big kiss. I could taste our juices on her lips. I told George that I didn't know if Jill would go for anything like that but that I would bring it up to her. I went back to my room. It was two am and I was worn out. I slept till nine.



It was Friday and I stopped at three more places looking for work with no luck. Then I grabbed a seafood dinner at pier 54 and headed home. When I got home, Jill met me in a tiny maid's uniform and crotchless lace underwear. She was horny and ready to take me to bed. I was ready too, even after what had happened the night before. Thoughts kept going thru my mind of my beautiful wife getting gangbanged by a bunch of virile young studs. I was rock hard before either one of us touched my manhood. Jill looked at it and smiled, "It looks like you missed me."



I fucked her long and hard but my mind kept thinking about what I was going to ask her to do. When I came, I stayed hard. That didn't happen very often these days but I kept fucking her till I filled her with my second load. Jill was totally satisfied too. "Maybe I should send you away more often," she said with a smile. We cuddled and slept well. The next day was Saturday and we spent it together. I told her that I had not had any luck finding work. Then I told her about meeting George. I didn't tell her about fucking his young wife. When I got to telling her about what George said his friend was looking for, Jill's jaw dropped in shock. "Are you suggesting that I should make that movie and have sex with several young guys while it's filmed?" I reminded her about how much money trouble we were in. "Think about it. If you say no, I'll never bring it up again. It would get us back on our feet and save the house. Whichever way you decide, just remember that I love you very much."



She didn't say a word about it all the rest of the day. After we had gotten into bed, she sat up, "If you want me to do it, I will." I replied that it would get us out of trouble but she had to be willing. She nodded her head yes and said, "Fuck me." First I ate her out then I fucked her, making sure that I totally satisfied her. "I love you so much, Jill."



The next day I called George's friend and got the details of what he wanted. He arranged for me to get three cameras to put in fixed positions and one for me to hold and take film of the action. He pointed out that he wanted the guys to look as young as possible but that they had to be at least eighteen, with proof, and that they had to sign waivers as Jill did also. I went on the Internet and started looking for the guys. They had to be good looking, look young and be willing to be filmed having a gangbang with an older woman.



Over the next week I found three that fit the bill. They all looked like they could be in their late teens. I told them that it was a fantasy of Jill's. I told them that the film would be edited so that no-ones face could be seen. Even though that was not true, it was how I got them to be willing to do it, and without being paid. They were doing it just for the fun of gangbanging Jill. I told them that they all had to sign a release. I arranged for them to come to our house the next Saturday night.



At eight o'clock that evening they started to arrive. I had Jill dressed in a very sexy outfit with a lot of cleavage showing and her ass cheeks sticking out below the bottom of her skirt. John was first. He was a five foot six inch surfer type. Bill arrived next. He was six foot and very slim. The last to arrive was Nick. Nick was about six one, muscular and almost as black as coal. Jill looked at me and whispered, "Do you really want me to be fucked by a black guy?" I told her that the guy paying us had insisted on it and that I was OK with it. "All right," Jill replied. I introduced them and Jill kissed each of them hello. They all fondled her tits as she did. I could see her nipples hardening. I told them that I would film each of them arriving again. Then I would follow them into the bedroom. After that, they should let nature take its course and have a fun time. I told Jill to let them take the lead and to do whatever they told her to do. "OK, let's do it."



The guys went back out. I started the camera just before the doorbell wrung. Jill answered it and John came it. Jill went to him and gave him a big kiss. John reached around and slid his hands under the back of her skirt and grabbed her ass cheeks. The doorbell wrung again. Jill opened it and Bill and Nick were there. They came in. Jill went to Bill first and kissed him. Bill reached out and tweaked Jill’s tits making her nipples get even harder. Nick took her by the arm and pulled her to him. Jill gave me a quick look and I nodded my head yes. Nick leaned down and they kissed hard. Nick ran his hand under the front of her short skirt and between her legs. Jill lifted one leg and spread them as Nick's hand slipped on to her mound and a finger slipped between her pussy lips and rubbed her clit. Jill moaned and kissed his black lips long and hard. "My husband is out of town over night. I'm glad you guys could come over and visit me."



Jill took Nick's hand and led him to the bedroom. The other two followed close behind. Once they were in the bedroom John told her, "Do a sexy dance for us and strip out of those clothes." Jill went over and turned on some music. She started swaying and shaking her tits. She pulled down her top and cupped her boobs in her hands and rolled her nipples between her thumbs and fingers. Then she pulled everything down and stepped out of her outfit. She spread her legs and rubbed her freshly shaved mound as she continued to dance for the guys. The three guys were standing there and Nick spoke next. "Take our clothes off." Jill worked back and forth among the three guys till they were all nude. Bill was rock hard. John was semi hard and Nick was limp. Nick put his hands on Jill's shoulders and pushed her down. "You know what we want, Slut. Get the fuck at it."



Jill looked at me again and I motioned for her to continue. Jill reached out and touched her first black cock. Then her lips encircled the head. Her natural urges took over. She took as much as she could in her mouth and she slid it in and out of her mouth while sucking hard. You could see her cheeks pull in as she sucked. Jill had never been able to deepthroat, to my dismay. She licked up and down the outside of his shaft and even sucked his balls into her mouth. Nick was fully hard now and was about the same size as me at a little more than six inches with medium girth.



John pulled on her arm. "Come on Bitch. You gotta do all of us, not just his black meat. Get over here. You may be older than my mother but I'm still going to give your cunt and throat a good fucking." John was the smallest guy but he had the biggest equipment at a little over seven inches and almost as thick as her thin wrist. Jill gave John the same that she had given Nick. Bill was next. He was the smallest, thin and no more than five and a half inches long. He almost dumped his cum in the first minute Jill sucked him but when Jill felt that he was about to blow, she stopped. I was moving around and in and out and zooming in for details as Jill sucked the three young guys who, in the movie were imagined to be in their mid teens. The three fixed cameras kept rolling. The best shots would be selected in editing.



John got on the bed. "Get up here and ride my dick." Jill climbed on the bed and slid her wet pussy over John's shaft till she was sitting on his lap. Then she started rocking her hips, sliding his cock deep inside her. Jill moaned in pleasure. Nick got on the bed at John's head and presented his prick for Jill to suck. It was the first time Jill had ever had two cocks in her at the same time but she eagerly complied. The three of them fucked for a couple of minutes. Bill and I watched as Jill was double fucked and I recorded the action. I handed Bill a tube of lube and pointed at Jill’s ass. He got the idea. He put some on his hand and rubbed it on his cock. He put some on the tip of his finger and reached over and rubbed it on Jill's tight little puckered ass hole.



Jill stopped and pushed his hand away. I nodded for Bill to continue. Jill and I had only done anal a few times and she did not really like it. Bill pushed his lubed finger at her butt again. She could see me and I mouthed, "Do it" to her. She stopped fighting it and Bill slipped his finger in her ass. After finger fucking her ass for a few seconds, he replaced his finger with his cock. John held her still. First just the head pushed in. Jill cried out, Owww that hurts." Another push and half of his cock was in her bumm. Tears were in her eyes. One more push and he was fully in. He just held it there for a minute and then slowly started fucking Jill's ass. John started fucking her again too. Soon Jill started sucking Nick again and pushing back against the two cocks in her holes.



The feeling of her two holes being filled at the same time, with just a thin membrane separating them felt better and better as they continued. The guys tried stroking into her at the same time and also one going in as the other was going out. She didn't think she would, but soon Jill felt an orgasm coming on. It hit her hard. It was one of the strongest ones she had ever had. John unloaded in her cunt. Bill rolled her over so he was on the bottom, still in her ass. John moved up to her mouth and Nick moved to her cunt. Jill sucked John's cum covered cock while Nick and Bill fucked her holes.



Bill was next as he filled her shit tube with his cum. They rolled over again so she was on top of Nick. Bill pulled out and moved to her head. She pushed him away and sharply told him NO. Bill took a handful of her hair and pulled till she opened her mouth. "Suck my fuckin' cock like a good slut. Clean all that cum and shit off of it, Whore." She gave up and opened her mouth and Bill's cock went from her ass hole into her mouth. Jill made a sour face but let him fuck her mouth without any further complaining. Nick saw that her ass hole was still gapping open and took advantage. Nick put her on her stomach on the bed and climbed on her back. It didn't take much effort to get his prick in her ass. She could tell that it was going deeper but it no longer hurt and she started to realize that she liked it. I spent a lot of time filming Nick's black cock sliding in and out of Jill's snow white ass and hearing Jill moaning in sexual pleasure. I almost shot my wad in my pants just watching. After he filled her ass, she did not resist sucking him clean.



The orgy continued till all three guys had shot a load into all three of Jill's holes. Jill had lost count of how many orgasms she had. Finally everyone was worn out. I had almost two hours of recordings on each of the four cameras. There would be plenty of hot fucking to make a good MILF gangbang movie. The guys dressed and left. Jill stood there with cum dripping out of her cunt and ass hole and running down her legs and a little smile on her face. She looked at me and said that there was one more thing she needed. "I need you to fuck me now and tell me that you still love me." Her holes were stretched and sloppy but I was happy to do what she wanted.



I put Jill on her back and lifted her legs up over my shoulders, giving me good access to both of her bottom holes. I alternated, shoving my cock fully into her cunt and then up her ass and then back again. Back and forth for about five minutes till I finally shot a load in her ass along with the three other loads that were already in there. Without me asking, Jill moved around and sucked my cock clean. "Yummm." I looked at her and said, "Jill, I love you very much and I always will." We went and slept in the guest room because our bed was so messed up and wet with cum puddles.



The next morning while eating breakfast, Jill looked at me, "Dan, I have to tell you something. Last night I was nervous at first, but I ended up really liking what we did. My holes are sore and my jaw aches but I want to do it more times." "I was hoping you would say that Jill, because I was never so turned on and I want more too."



Well the movie turned out really good. The finished film ran over two hours. We got paid the full eight thousand and were told that the producer thought it would be a real big hit and that he wanted us to make more films for him. He sent me four copies of the movie. Three of them had blurry spots on all the faces. I gave them to the guys that were with Jill. The fourth one did not have the spots. That one was for us and was also the way that the movie was sold to the public. If the guys ever happened to see the public version, we had the releases. Jill and I enjoyed watching it while we planned the next gangbang that Jill is going to have.









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