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This is going to be a 3 or 4 part series of our story to embracing cuckoldry. I’ll warn you that the vibe of our story changes. It starts with a sweet, romantic threesome with an old friend, and the final part will probably have trigger warnings on it for roughness. It will get heavy into the humiliation aspects of the kink, which is not something I have learned to enjoy. Perhaps this audience will enjoy it, but I do warn others that this experience almost ended our marriage before we moved past it, even though it’s better than ever now. Once I catch up, I will also write some more extreme fantasies that have grown out of this as I’ve shared these stories with a few of you online. Feedback is very welcome – it will motivate me to write more if I know people enjoy it, and I always appreciate constructive criticism too. I have enjoyed reliving these moments with people online, in fact that was a major factor in our relationship healing after things went too far, so please don’t be shy. And now, on with the story.
It still doesn’t seem real how much has changed in the last few years. For the first decade of our marriage, my wife struggled with a lot of hormone problems that impacted our relationship and especially our sex life. We both came from very conservative backgrounds to begin with, and a lot of the anti-sex shaming still stuck with her too. I thought it was hopeless because I had tried everything but she didn’t see a problem and wouldn’t work with me about any of it. By the time we were in our mid 30s with a few kids, I was starting to not be able to tolerate how I felt any more, but I felt more stuck than ever.
Something changed a few years ago after I told her that I had gone looking to fulfill my needs somewhere else. We both went to counseling, she finally agreed to see a doctor and get help for some of her issues, and a little hormone supplementation and ADHD treatment really turned everything about our relationship around. But it also really helped that she started reading smut with some of her friends. It used to be that I had to explain half the cards in Cards Against Humanity to her and she was shocked that anyone knew about certain sex acts. But now she was learning all about BDSM dynamics, knotting, getting Eiffel Towered, etc. and telling ME about it. I had to act like I hadn’t watched videos of most of these things before, because she would not have approved at the time!
In the meantime, I had started developing a cuckold kink because I just wanted to see her want something so badly. I wanted to see her enjoy sex and receive pleasure at any cost. I also have a huge oral fixation, so I had always wanted to go down on her more, eat her ass, etc. but she always avoided it and wouldn’t engage. So what really kicked things off is that she was opening up about receiving pleasure, and getting over any insecurity to let me give it to her. Suddenly those walls were down, and she started asking for it. A lot. This is how I first brought it up.
We would spend a lot of time during sex with me eating her ass, while she would use a vibrator. I would alternate between that and fucking her in doggy style, and I started making comments that I wish she could experience both at the same time. I started using a dildo on her, and then saying it would be great if I could use that while eating her ass, AND stimulate both her nipples at the same time. She liked this idea and we kept wanting to add more simultaneous stimulation, and we started openly fantasizing about an MFM threesome. I definitely used to have some insecurity when we were dating, so she was cautious about much I really wanted to see her pleasured by someone else. The real life-changer was one night when she was especially wet and warmed up, and I squeezed myself into her pussy while the dildo was in there too. She LOST HER MIND. Her first time experience DVP, albeit with a toy. She was committed now: she needed to experience two cocks, with two sets of hands and mouths exploring her body.
We talked and researched online about the lifestyle (me still pretending I hadn’t already been into this for years). We talked a lot about boundaries and how we were going to feel about this. We even started looking online for potential partners, thinking we wanted a stranger a certain distance from our home, thinking we would meet somewhere safe and anonymous. But then we ran into an old friend, Ryan.
Ryan and Ashley dated in high school. He had dated a few of her friends too. It never got serious, but they went to Prom together and he definitely made an attempt at feeling her up and going further, but she wasn’t game back then. Events since then had made us see him as a “failure to launch” situation, you might even say loser, but as I thought about the details I realized he was perfect. We knew he had been into her before, she had always thought he was really hot, and we all had some rapport. We also knew that he would never want our shared circle to find out, so his parents never found out. He was living with them and had to play the role of “good Christian son”. We had run into him a few towns overs, and had a great time catching up, even just for a few minutes. We said we’d get together more, like everyone says but never means. But I told Ashley to text him. It got flirty right away, and escalated for a couple of days. They were sending thirst traps back and forth and openly sexting, so we pulled the trigger: she told him that I knew about it, and that we had been looking for a third, and that we thought he was perfect.
His response? Fuck yeah. BUT DON’T TELL ANYONE. Perfect.
The end of the school year was coming up, and we decided to take advantage of one of the last chances for a while to have an empty nest while the kids were at school. We invited him over about a week later, and my wife just got giddier as we got closer. She went to work getting everything super clean. The nice bedding. Trying out new lingerie. We talked about it every chance we got. She was so excited, the kids even thought something was up, of course they’ll never guess what.
The day came. She spent ages on her makeup, put on the lingerie we had picked out, and a robe. We started feeling anxious when he was a little late, but then he came. We invited him in, all casual, had a glass of wine in the kitchen, but the conversation was just awkward. I said look – we don’t have to make this awkward. We all want the same thing, so let’s stop pretending we don’t all just want to get into it. Babe – show him the bedroom, I’ll bolt the door… (her parents had a habit of coming over unannounced). Clearly we just needed to acknowledge what it was, because everyone immediately moved. We all wanted this.
We got into the room and she was already standing in front of him, smiling ear to ear, just beginning to shed the robe. We had picked out a red number. It covered her tummy enough – she had lost a lot of weight since getting her sex drive back, but was still self-conscious about her mommy belly. But it was lacy and had great lines. It held her breasts just right, it framed her ass nicely and once her legs were spread, both her holes were nice and accessible without having to remove anything. You’d think it was her first time having sex the way she was giddy and nervous, giggling and smiling at us all the time. Ryan’s cock was pretty comparable to mine. A little longer, a little less girthy, but pretty close. We were both cut and curved the same way.
Ashley went right to work on his cock. For being relatively inexperienced, she gives GREAT head. She swapped back and forth between us. I think she was still very nervous about this going wrong if I got jealous. But she got a lot of praise from both of us, and joined in. She really liked how slutty this was and kept asking us if we liked that she was willing to get double teamed. She was really liking all the dirty talk. She started working our balls, and getting sloppy, the way I like.
I told her to get on all fours on the bed, and I could eat her out from behind while she kept sucking on him. We got into a rhythm again, and she was really going to town on him, moaning and asking him if he liked things. She loved all the affirmation. She was a little shocked that I would eat her ass in front of him, and then asked him if he liked that about her too. This was so good for her self-esteem and shame.
I could tell she was really starting to get overwhelmed by desire the way she was gobbling his cock and balls. I asked if she wanted to ride me and keep sucking him, or if she wanted him to come inside her: she said it was time for DVP! He clearly agreed because he was already going for the condom. She mounted me while he finished putting it on, and was SO wet. I thought it was going to be a piece of cake for both of us to get in her, but it turns out with real cocks it’s not so easy. We were having a hard time getting him inside her when I was already in there. In hindsight, I was the one who had experience slipping a cock in from that angle, I should have been there, but I think she felt more comfortable facing me. We tried for several minutes, but it kept hurting a little too much for her, or just feeling awkward. So I slipped out, and just told him to get in there and get warmed up again.
She LOVED it. This was the first real cuckold moment (a word neither of us had actually dared to say, and wouldn’t until much later). I was lying beneath her, looking her right in the eyes, while she got penetrated by her high school crush, and he just started going to town. He went harder than I usually do right away and she liked it. I think she really felt the little bit of extra stroke length too. I asked her if she liked it, and she said she loved it. Checked in with me that I was okay with this, so I just heaped on more praise: this was HOT and I loved it. After a minute, I started sliding out from underneath her. Ryan asked if I wanted a turn or a new position, and I just said, “I get to have her all the time – you’re both loving this – just keep going!” It felt awkward that they both thanked me, but I was right – they really were both loving it, and I was too.
I just stood there watching them for a little bit. After a little while they wanted to change positions, and asked if I wanted in again. I asked if she liked how hard he was going by himself and got a very enthusiastic “YES!” Turns out she had actually already cum, and apparently it was a pretty good one. Most of the time she just has one and she’s done. Sometimes I can give her two, only one has she had three. I asked if she could cum again and she thought she could. She rolled over on her back and spread her legs, and told him that yes, he could go harder. There was a moment of silence and hesitation and she said, “please… please go harder…” and looked at him with the most lusty eyes.
He entered her in a push up position and starting really going to town. There was a lot of moaning, her hands running up his back and through his hair, and then down to his hips to help him set the rhythm. They stayed like this for a long time, as her whimpers slowly built up and climaxed, LOUDLY this time. She started sounding extra wet, and we realized a few seconds later she had squirted a bit on the bed. She had only done this once before with me when we tried a magic wand for the first time. She wasn’t even using a vibrator with him. I asked her if she wanted one to make it even better and she just told him to finish however he wanted.
He didn’t need to be asked twice, lol. He lifted up both of her legs, one a little higher than the other, and just started fucking pounding her even harder from above. She started squealing and moaning so loud I thought she was doing it for his benefit. I thought from their rhythm he was getting close, but then he pulled out. He ripped the condom off and told her to go get on her knees again. He looked at me and said we should finish on her face together. It turns out she didn’t need to be told what “bukkake” was this time! She knew exactly what to do. On her knees, face up to the ceiling, tongue out, moaning to express her thirst. We both went over, and he had kept himself pretty close, he started cumming in about 10 seconds, long, thick ropes with perfect aim, all over her face. She loved it, and that just pushed me over the edge too. When the ropes stopped, she pulled us in and gave each of us a few seconds of sucking to clean up and finish us.
I later found out she had her hardest orgasm right before he pulled out. She thinks she might have had 2 in that position, but said it was all just blending together at that point. I think some post-nut clarity hit him, because he was pretty quick to ask for a towel, put his clothes back on and start heading out. She and I just stayed in bliss for a while… We rested on the bed, almost in silence. We checked in with each other that we both really loved the experience, and eventually went to take a shower. We went out for lunch and just stayed at home – she needed a rest and was almost in shock at what had happened. She was very concerned about how I felt, if I had really liked seeing her cum that much with our friend, and if I really didn’t think she was “too slutty”. Oh no, my dear – I loved how much you let your slutty side out. One thing was for sure: we both wanted to do it again.
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