Category: Hookup Stories

Seducing and Older Woman – Part 2

Post author By Admin
Post date January 22, 2021

So I told you all about the time that I got the chance to try and seduce my mother’s best friend when I was 18 years old. I had been infatuated with this woman for years and had always fantasized about her. I was newly legal and our two families had decided to take a vacation together. We were all down by the lake at the vacation rental, except for my mother’s friend. She was back in the cabin by herself. I made my way back to innocently use the bathroom when I walked in on her masturbating with a massive magic wand. She just looked at me and finished and I left the room. I was enthusiastically jerking off to what I had just seen in the bathroom when the door opened up and she walked in. The way she figured, she had just given me a show and now it was time for me to give her a show. She just stood there and watched me jerk off until I came and she caught all of my spunk on her foot. That was just the first day of us all being together, and I needed more of her.

She was gorgeous

Like I said before, this woman was gorgeous. She was a tall brunette with an amazing body. Her tits her perfect and I was constantly staring at her ass. The way that it moved under her clothes could get me hard in a matter of seconds. I was incredibly happy about use masturbating for each other, but I really wanted to take things even further. I needed to have sex with her and I had to figure out how to make it happen. I spent the rest of that day wondering what would work. Maybe if I could get her alone and horny enough, she’d have no option but to fuck me. Maybe if I managed to walk in on her again, she’d ask me for a little bit of help. The possibilities ran through my mind and I had no idea which ones would actually work. All of my working plans dissolved that very night. The parents were all sitting around the fire outside and drinking. I was by myself and watching TV in the living room. The time of the night came for everyone to head to bed and that was when I was treated to another session with this amazing woman.

It was just us

I sat there and watched everyone file past me and head to their rooms. Everyone except her, of course. She simply called to her husband that she would be up to bed shortly and watched him disappear into the bedroom. Then she jumped down onto the sofa next to me and told me that he was going to be passed out in five minutes. I had no idea what to expect. I know that I was hoping that something else was going to happen between us, but I had no real reason to believe that it would.

“You had fun earlier, didn’t you?” She asked with a smile.

All I managed to do was nod and turn my body to face her on the sofa. I’m almost positive that I had a surprised and stupid look on my face.

“Well, then how would you like to do me a favor?”

“Of course, anything.” I said, knowing it was stupid.

That was when she leaned in really close to me and started to whisper in my ear. I could feel her breath on my ear and it made my dick shoot into an erection.

She wasn’t what I thought

My entire life, I thought of this woman as an authority figure. She was a mother and a friend of the family. She was able to yell at me when I did something wrong that my mother wasn’t there to catch. She was basically a grown up, just like all of the other adults that I knew. That’s why it was surprising to me when she told me what she told me.

“Everyone thinks that I’m a good girl.” She whispered into my ear. “I’m not, though.”

She smiled wide and leaned back from me. Then she took my hands into her hers and looked me right in the eye to tell me that I had become a very attractive young man. Then she leaned in again and told me in a quieter voice that she enjoyed fantasizing about me over the past few years whenever she had sex with her husband.

“The problem is that he thinks I’m too good for the things that I really want.” She said.

“What do you mean?”

I had no idea where this was all going and my brain was rolling around in my head after hearing that she fantasized about me. It was even more shocking to hear that she did it when she was having sex with her husband. That was something that I couldn’t even process. I was the one who was supposed to fantasize about her. She was unattainable to me and here she was, tell me that she wanted to do all of the same things that I wanted to do to her. I didn’t know how I was supposed to react in a situation like this and I was even less equipped for what came next.

She needed to get dirty

“Well, what happens when you have kids is that most men start to look at their wives as mothers instead of their wives. I know you don’t know what that’s like, but it’s not very fun.” She told me.

“Oh, okay. I think I get it.” I said.

“I love to have sex, like really, really love it. The thing is that I need it to be a little more extreme than most women. I don’t like the things that most girls like.” She said with a smile starting at the corner of her mouth.

“My husband won’t do the things that he used to do to me because he see me as the mother of his children now. Do you understand that?”

That made total sense to me and I told her that. I completely understood where she was coming from in that moment. This was a woman who was starved for the things that really made her feel like a woman and it was driving her insane. That must have been why she fantasized about me. She could tell that I wanted to do all of those filthy things that he husband used to do to her.

She let it all out

It was at that moment that she decided to just go for it. She had already crossed every line that there was and it was time to cross the finish line. She leaned in to me and kept on going until I was on my back on the sofa with her on top of me. Then she placed her head against mine again and whispered, once again letting her breath play across my neck and ear.

“I want you to fuck my asshole like the horny little boy that you are.”

That was all I needed. My cock almost exploded right there. I could feel it pushing against her pelvis. It felt good. It was throbbing and I could tell that I was already leaking more precum than I had ever expelled in my entire life. All I could do was nod and stammer out an okay. As soon as I did that, she took the initiative. I felt her hand open up my pants and pull out my dick. Her eyes got wide once her wrapped her fingers around it felt how thick and hard it was for her. It must have been the first time in a very long time that someone was that excited to fuck her. She was clearly appreciative of my reaction and she acted accordingly. I watched her face disappear as she moved down my torso to take my cock into her mouth. She kept one hand wrapped around the base of my shaft and slid her head up and down it. It was the warmest and softest mouth that I’ve ever felt wrapped around my dick and I still like to the think about the way that it felt on me for the very first time.

More next time

This was an amazing woman and an amazing hook up. She clearly needed it just as much as I did. I’m going to come back to this story next time. I want to make sure that I can share as much of it as I possibly can. I also don’t want to get any of the details wrong. They’re pretty important in this one and I want to give it all of the attention that it deserves. Until then, just think about all of the married mothers out there that need help just like this one did.

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Seducing an Older Woman

Post author By Admin
Post date January 17, 2021

I used to have a huge thing for older women. This was back when I was about 18 or so. There was just something about the experience they had that made me crazy. I wanted to get as much of it for myself as I possibly could. I tried to seduce many older women back there with varying degrees of success. I thought I’d share the story of how I managed to seduce my mother’s best friend. I was definitely 18 and she was in her late 30s, I believe. It worked better than I ever could have imagined and I still think of it with a giant smile on my face.

We went on vacation

It all started when we all went on a vacation. It was me and my family along her and her family. We were going to be in close quarters and I knew that it was going to be next to impossible to not be constantly hard as a rock around her. I had always had a thing for her. She was a tall brunette with perfect boobs and an amazing ass. Any time I had friends staying over, they all took turns just staring at her. That’s how hot this woman was and I had to do something about it. Sure, she was married and had kids, but still. I was 18 and I needed her. I knew that I had to figure out how exactly I could get something from her. At the very least, I wanted to see her naked. That was pretty much my goal for the vacation. I didn’t care if I had to walk in on her in the shower or catch her changing in her bedroom. I had to see her naked, no matter what it took.

My first chance came quickly

I never thought I’d get to see her naked pretty much as soon as the whole thing started. We had all arrived at the vacation cottage that morning and everyone unpacked. I took every opportunity that I passed by her in the hall to check her out. She was looking tired, but hotter than ever. She has this tiny skirt on and a tank top and really showed off her perfect tits. Anyway, we all got together and both families were settled and decided to head down to the lake for a quick swim before dinner. Both families headed out but it wasn’t long before she said she was heading back to the house for a few minutes. No one thought anything about it and twenty minutes passed. I was having too much fun in the water to really notice anything, but I suddenly had to use the bathroom worse than ever before. I ran out of water and up to the house without saying anything to anyone. I made it to the bathroom just in time and did my business. I make my way out of the bathroom and that’s when I heard it.

She was gone for a very good reason

The sound was pretty quiet, but I still heard it. I had to follow what sounded like low vibrations in one of the rooms and the closer I got to her room, the louder it got. That was when I saw that the bedroom door was open just a crack and the sound was clearly coming from inside. I pushed the door open and that’s when I was greeted to a site of this gorgeous MILF naked and on her back with her legs spread wide. She was going at her pussy with a giant vibrator. Now that the door was open, I could tell that it was a loud and powerful thing that was clearly doing the job for her. I could immediately see why she needed to be completely alone to use it. I must have made a noise because her eyes shot open right as it was clear that she was starting to cum. She looked shocked at first, but seemed to realize it was me, rather than her husband or one of her kids. I really mean that she was right on the edge and she just looked me in the eyes and started cumming right there on the bed.

I was frozen

I had no idea what to do. I had no expectations of this happening and I certainly wasn’t hating it. I just stood there at the door for a few minutes and watched her try to catch her breath with her eyes closed. It was clearly a very nice orgasm. Then she finally opened up her eyes and looked at me.

“It’s okay that you watched me, but let’s not tell anyone about this, okay?”

I just stammered a yes and started to back out of the room.

“By the way, you owe me a show later. Just because I like to be watched doesn’t mean that I perform for free, honey.”

She was smiling wide and turned around to face away from me and recover. I just closed the door and ran right back to the bathroom. I can’t tell you just how hard I started jerking off right then and there. I was on the toilet with a massive erection and I was working it harder than I had every jerked it before. I was even running the water to lather up the soap for lube while I played back the images of her cumming over and over again.

I must have been loud

Either she instinctively knew what I must have been doing or the sloppy sound of the soap and stroking gave me away. Either way, I was rounding the corner when the bathroom door slowly opened. I panicked and immediately stopped, but then I saw that it was her. She was still completely naked and smiling at me. She slowly slipped into the bathroom and closed the door behind her.

“I guess you’re ready, then.” She said.

The rush of excitement and arousal slammed through my entire body. Once again, I had no idea what to do. I think that I must have just nodded to her and grabbed right back onto my dick. I had never been watched before in my entire life and I still don’t know if I actually like it. I still had to do it, though. I watched her and now she got to watch me. That was just fair. I started stroking all over again and looked up into her eyes while I worked. That part really turned me on, but I also felt totally open and embarrassed at the same time.

She knew I was close

She didn’t really waste any time in making sure that she enjoyed this as much as she possibly could. She could probably tell that I was getting close by the way that I was jerking off faster and faster.

“That’s a good boy, keep going.” She said with a smile. Then I felt something brush against my calf. I looked down to see her naked foot making its way up my leg, touching my skin the entire way.

“Don’t worry about that. Look me in the eye, honey.”

I did as she asked and looked right at her and I felt my cock start to explode. The cum just shot out all over the place and I noticed her look down to her foot right before I felt her toes start sliding up and down my shaft. I let my dick go and leaned back while she stroked me through the orgasm and kept going until I felt every last drop of my cum leave me. I fought to keep my eyes open so I could keep looking at her and she never stopped smiling.

“Looks like we made a mess.”

I looked down to see her foot absolutely covered in cum. I guess it wasn’t just shooting all over the place like I though. She knew exactly what she was doing. She caught it all right on her foot and made sure she didn’t miss a drop. The she simply grabbed some toilet paper from the roll next to me, leaned forward, and wiped it all off of her. She slipped the tissue in between my thighs to drop it in the toilet, kissed her first two fingers, then pressed them to my rapidly deflating cock.

She said “Good job.” Then she just turned around and walked out of the bathroom, closing the door behind her.

More next time

This was just the beginning of the vacation and I had no idea that any of this was going to happen. I couldn’t have even come up with it in my biggest fantasies. It happened, though, and that wasn’t the end of it. I’ll some more to say about it next time. It was a great vacation and I found out that this much older woman wanted me just as much as I wanted her.

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Hooking up with a Freak – Part 4

Post author By Admin
Post date December 29, 2020

So, there I was behind this married freak while my regular hook up face fucked her with her strap on. I wasn’t going to let them have all of the fun, so I decided to relieve the married cum slut of the giant butt plug in her asshole. I was careful to pull it out gently to not cause any real damage or pain. The thing about butt plus is that the asshole likes to hold onto them. That’s the way that they’re designed. If you don’t pull them out slowly, then you can be in for a whole lot of problems when you really don’t want them. Once it was out, her asshole gaped for a few seconds. She had been wearing it all night long, so it made sense. I had to wait for a bit for it close back up enough, but I made good use of my time. I ran my fingers over her dripping wet pussy and used the juice to lube up her ass again. I could tell that I had to start moving faster because my regular hook up was getting closer to cumming and I didn’t want her to go on her own this time.

Strap ons are made for it

If you ever buy a strap on, make sure you get the high quality ones. These strap ons are designed to give the woman wearing them as much pleasure as possible. They curve under the shaft to rub against the clit while they’re using them on someone else. They can make the wearer cum just as hard as the person actually getting fucked and that’s what makes them so much fun. It was also why she was about to cum and I had to catch up. I got on my knees and shoved my cock deep into the married slut’s asshole. It was so loose from the plug that I didn’t have to push hard at all. It just swallowed me right up and that’s how I like it. I just start jackhammering away, trying to cum as quickly as I could. I also made sure to order the married slut to rub her clit while I worked. I told that I knew a slut like her was dying to do it and she obeyed. She was being fucked in her mouth and her asshole while she fucked her own pussy and it was obvious that she was loving it.

Everyone came together

If I needed more proof, I got it very shortly. My regular hook up closed her eyes and started cumming while she continued to face fuck the married slut. Seeing it must have pushed her over the edge and I felt her asshole tighten as she started to scream and moan in orgasm. That was all I needed to blow my own load deep inside her freshly stretched out asshole. All three of us came at the same time and you just can’t get any better than that.

A night of cuddling

The thing to always remember about a cum slut who loves humiliation is that you have to give them aftercare. They go through a lot of emotions during their sessions and they need to be taken care of afterward. Both my regular hook up and I took turns cuddling with her and telling her how great of a job she did. We finally ended up falling asleep that night in my hook up’s bed. I was on my back in the middle with both girls sleeping on my chest and I can’t think of a better ending that that.

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Hooking up with a Freak – Part 3

Post author By Admin
Post date December 28, 2020

We had just gotten to my usual hook up’s apartment and she immediately told her married friend to take off all of her clothes. She didn’t even give her a chance to settle in and that was all part of the experience that she was giving her. Her married friend was a fetishist and considered herself to be a cum slut. They’re a really fun subset of BDSM that gets off on being insulted and humiliated with sex. They feel that they crave sex so much that they need to be punished for it. It gets them off and it was exactly what this woman needed. She wasn’t getting it from her husband at all. He was just incapable of being the sexual partner that she needed. She had confided all of this to us earlier that night and we were intent on taking care of her. She clearly had a need and she was desperate to have fulfilled. We were going to do that for her and her husband never needed to know a single thing about it. If he couldn’t take care of her, then we would do it and she would be able to go home happy and satisfied afterward.

She did everything she was told

My regular hook up knew what she was doing and she never let up for a single second. She told her married friend that sluts don’t have to wear clothes because they’re always taking them off anyway. That’s’ why she was currently naked and standing in the middle of the room with nothing touching her body but the big butt plug in her asshole. My hook up told her that a slut’s place was on her knees and the married girl knelt down immediately. She was into it as deeply as she possibly be and it was obvious that she was being fulfilled on a level that she hadn’t experienced in a very long time. That was when I realized that my regular hook up was sliding off the skirt and panties that she had been wearing all night long. She stepped right up to her married friend and lifted her right leg to rest the inside of her kneed on top of her shoulder. The grabbed a handful of her hand and explained to her that sluts can’t stop themselves from eating pussy when it was right in front of them, no matter how sweaty it was from dancing all night long.

She seemed to agree

The married woman nodded her head in agreement and she couldn’t seem to take her eyes off of my hook up’s naked pussy in front of her. I just stood there and enjoyed the show as my hook up pressed her married friend’s face right into her crotch. Her eyes closed and she let her head fall back as her friend started eating her sweaty pussy for her. It was pretty obvious from watching her reaction that the married girl was just as good at eating pussy as she was giving blowjobs. I was able to experience that blowjob skill for myself just an hour earlier. She had taken me out into the alleyway next to the club we were at to kneel on the filthy asphalt and suck me off right them and there. That was how I knew that she was a cum slut. She wanted to be used and her husband would never be able to do that for her. She was bored and she was desperate for the kind of sexual pleasure that she hadn’t felt in many years.

My hook up guided her through it all

The pussy eating certainly went on for a long time and they both seemed to be enjoying it. I could see the way my regular hook up’s body was moving and I knew that she was getting close to cumming. She asked her if she liked eating her sweaty pussy and the married women mumbled an affirmative and nodded her head. The vibration from the mumbling was just too much for my regular hook up to handle and I watched her cum right then and there. She pressed her married friend’s face even deeper into her pussy and held it there tight until she came all over her mouth and started bucking in her legs and shoulders. Then she pushed her face back and stood there with her leg over her shoulder until she stopped shaking from the orgasm. She caught her breath and looked down at her and pushed her back hard so she landed on the floor. She told her that she was a bad slut for making her cum without permission. This is where all of the humiliation really started and I could see that the married women was eating it all up and loving every second of it.

It was time for the punishment

My regular hook up ordered her friend to get on her hands and knees on the floor and kept telling her that she was a naughty slut for giving her an orgasm. She told her to stay exactly where she was and disappeared for a minute in her room. Then she came back with a long whip in her hand and smirk on her face. She told her that if she couldn’t be trusted to ask for permission to make someone cum then she was going to be punished until she remembered. She moved up right behind her and let the whip fly. She swung her arm and let it crack painfully against her naked ass. The married friend worked hard to keep her screams silent, but it didn’t last long. She started moaning and sighing with every crack and she was only getting louder. I was standing by this whole time and just enjoying the view, but I knew that I had to do some work as well. I simply told her that is she couldn’t keep her mouth shut then I’d have to stuff it with something.

I got my second blowjob

I opened up my pants and let them fall to them floor. I stepped out of them and stood in front of the married friend. She was making a lot of noise and I had to give her a reason to stay quiet. I slid my fingers underneath her chin and lifted her face right up to my dick. I didn’t have to work hard to get to start sucking me off just like she had just done in the alleyway. The sensations of her moaning in pain and pleasure made it feel good on a whole new level though. I just stood there and face fucked her while I watched my regular hook up whip her on her other end. It was a lot of fun and there’s no way that I would have ever traded that experience for anything else. Everyone was having fun and getting exactly what they needed out of each other. We went on for a while before my regular hook up decided she wanted a change. She dropped her whip and said that it look like more fun from my side.

We switched sides

I agreed to let her experience it for herself and pulled my dick out of the married woman’s mouth. My cock was dripping in her saliva and she was just smiling up as me. I moved to her other end and saw that her entire ass was bright red and starting to bruise. My regular hook up had done a very good job of punishing her friend. She disappeared into the bedroom again and came back a minute later with a giant strap on dildo belted to her. It wasn’t anything that she had every used with me and I was surprised that she had some toys I had yet to discover. She took my place in front of the married girl’s face and made her suck on that dildo for all that she was worth. That’s an especially humiliating thing to do to a cum slut and she was loving it. I was behind her now and I could see that her pussy was absolutely dripping with juice. There was a long string of it going from her clit to the floor and I knew that this was something she was never going to be able to forget.

More next time

I’ll have more to say about this night next time. There was just a lot going on and it’s a lot to share. I’m really enjoying remembering it all, though. It was a really fun night and I don’t think that any of us have ever been able to forget about it. It also wasn’t the only night that the three of us got together for it, but that’s a different story for a different time. I’ll have more about this one tomorrow and I’ll let you know how it all ended.

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Hooking up with a Freak – Part 2

Post author By Admin
Post date December 27, 2020

I just told you all about the benefits of hooking up with a real freak. It’s a really good time and everyone should do it at some point. I was just hanging out with my regular booty and her married friend when the new women decided to open up to me. It turned out that she was in a sexless marriage and she just couldn’t handle it anymore. Her husband just couldn’t keep up with her sexual desires and she was desperate for a release. I really didn’t expect her to take me out into the alleyway next to the club to blow me and swallow my whole load to finally get what she was missing. We just walked back into the club and she went to dance with her friend. I sat there by myself for a few minutes until I noticed something was going on. People kept moving in front of the two girls, but as the dance progressed, I kept getting glimpses of what was happening between the two of them. Seeing what they were doing gave me a pretty good idea that we were going to be doing a lot more than the blowjob that night.

They were getting very close

The first glimpse caught of them just showed the married friend turning her back to my other friend and grinding her ass against her. It was a common dance, but I could see the look on my usual hook up’s face. She was shocked at something, but not upset about it. People moved in front of them again and I lost my view for a few minutes. Then the floor opened up a little again and I could see that my usual hook up had the married friend’s skirt up and she was looking at something on her ass. I lost my view again and sat back. I had no idea what was going on, but it looked like it was a lot of fun. I got my last view of them and the married friend was whispering something into my usual hook up’s ear and they kept looking at me and laughing. I smiled and waved and that was it. I sat there for the rest of the dance and just waiting for them to come back. When the music ended, I found out what was going on.

They came back

The two of them walked back to the table and they were all smiles and giggles. My hook up asked me if the little slut next to her had told me what she had under her skirt. I said that I had no idea at all. That was when my usual hook up told her friend to stand up and show me what she had done. The married woman just stood up at the table, turned around, bent over, and lifted her skirt just enough for me to see. It was right there across the table. She had come out that might with a giant butt plug inserted deep into her asshole. It was being held in place by her tight, tiny panties and she had dancing with it in all night long. That also meant that she had it in while she was sucking my dick in the alleyway. I still had no idea if she had told my usual hook up about that or not, so I just kept it to myself. The girl turned back around and sat in her seat with a broad and naughty smile on her face for a few minutes.

My hook up spoke out

The girl that I usually hook up with leaned in and told me that the little slut next to her had told her that she wanted to show me something else when they got back. I didn’t know what was about to happen, so I just agreed and sat back. Then my hook up told her friend to spread her legs like the little slut that she was. She did exactly as she was told and spread them under the table. I could feel her knee brush against mine, so I knew that it had happened. My hook up told me that the little slut wanted to show me how hard she can cum when she’s so desperate for a good fucking. With that, my hook up slid her hand in between her married friend’s thighs and started working her clit with her fingers. Her arm whipped back and forth furiously and the married friend arched her back and started moaning right away. She tried to hide it from the entire club, but it was clear that it just felt way too good for that. She covered her mouth with her hand and came hard right then and there. She bucked and jumped and I could hear her scream under her hand.

Her fingers were dirty

After she stopped cumming, by hook up brought her hand up from under the table. The married woman was gasping for breath and sweaty. She was also smiling just as much as she had after sucking me off in the alleyway. I could see that my hook up’s fingers her drenched in her friend’s pussy juice and she had to do something. She just looked at her friend and asked her how she felt about her slutty ways getting her fingers all wet and dirty. The married friend just apologized with a smile and wiped them off for her with a cocktail napkin. Things her certainly getting interesting and I was more than happy to go along for this ride. My usual hook up just leaned back in her seat and asked me what we were to do with this little slut. I told her that I guess she’d just have to be punished until she got all of her slutty tendencies out of her system. I can’t even begin to explain the look of pure delight and pleasure that spread across the married girl’s face when I said that.

We brought her home

The club just wasn’t the best place for us anymore, so we all got a cab and made out way back to my hook up’s apartment. We were already halfway there when I realized that my hook up’s hand was back in between the married woman’s thighs. It was too far down to be working her clit, though. The best I could tell was that she was sliding the giant butt plug in and out of the married girl’s asshole. Her eyes were closed and her fists were clenched. She was clearly trying to take all of the pain and pleasure that it was giving her without making a single sound. It worked all of the way to her apartment when she pulled out her hand and we all made out way up to her place. I have been there plenty of times, so I knew about all of the toys that she had waiting for her friend. I was happy to play along and make sure that this girl got everything that she needed from us and it was obvious that my usual hook up was doing the exact same thing. She must have been hearing about all of her troubles for a very long time and she was finally going to do something about it. I could only assume that it was also the reason for her inviting me out with them. She knew what her friend needed and she also knew that I could help to give it to her. We were going to take control of her for the night and make sure that she left the next day fully satisfied and no longer missing a single thing that she needed sexually.

More next time

This was a really fun night and I want to get back into it tomorrow. I’ll have more details for you and I want to make sure you get all of them. If you ever come across a woman with a fetish, it doesn’t matter if she’s married or not. A fetish is a need that people have to get fulfilled. If their husbands won’t do it, then they have to get it somewhere else. You should never turn a girl down just because she’s not single. Marriages aren’t perfect and sometimes people have to get what they need elsewhere. If you’re willing to give them what they need then you can basically be a hero to them. They need what they need and that’s all that there is to it. Be open minded and willing to help out a married woman. If I hadn’t done it for this girl on that night then I have no idea what would have happened to her. She probably would have gotten totally fed up with her marriage and left it. I don’t want to say that I saved her marriage, but I certainly made it all a lot easier on her.