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My wife and I are friends with a guy that is in love with her since we were teens in school.
Back then he was in her class and they both got along really well since they both liked the same shows and anime. He never really made a move on her but he had expressed his feelings for her in a way. She said that they gave it a chance but it didn’t last. They didn’t even got to kiss before she told him that they would be better as just friends.
During that time I met her and a couple months later we started dating. I was really jealous at the time and when I saw that he was clearly in love with her, I told her to keep a distance from him. We were kids, I don’t know why I was so worried.
I guess it was some cosmic irony because a few years later my jealousy did a flip and now I was into cuckolding, I was now more than excited to show off my wife and kept wanting her to actually be with another man. She was very fond of the idea, not a first of course, but she wanted to do it with someone we liked and we could trust.
We were about 21 or so at the time so all the men we could find online for that looked a lot more focused on fucking her and not about the threesome/cuck part of it. Plus talking to older people just seemed a little dangerous. I was getting desperate and annoyed at the whole thing and that’s when I had this crazy idea. What about that guy that was on love with her?
Although she didn’t talk to him as much as back in school they were still friends. He was a part of her friend group too and even went with the group to hangouts but they never had a one on one conversation with each other.
So when I suggested him she had a lot to think about. In the end she agreed to be him our first time but only if was into her right now and didn’t care of her being in a relationship.
I looked at her with a assured look.
“Oh I promise you he won’t care at all about that”.
And right I was.
She texted him to make conversation and they clicked like they never got apart. After some time she started flirting with him in a joking tone and he did the same although more koy. She mentioned that the group was planning a cookout and she asked him he was going. He said yes and asked about her which she responded with “If you’re going I’m going”.
After some time he felt more comfortable about talking to her about more sexual subjects but never directly aimed at her, like he didn’t want to put himself between us. He was very respectful and a good listener.
It came a time where I asked her if she thinks that he would say yes to something happening between them two and if so if he would be ok if I was there too. She warmed him up to it and finally asked if he would want to do anything without her for real and he said yes, if she was okay with it. She then told him that I was okay with her being on a open relationship and if he wanted to do something some day then it would be okay for her.
The guy was over the moon. Apparently he was still a virgin and having the possibility to losing it with her was the best he could’ve imagined. Ever since that conversation he kept wanting to set a date so they could fuck but she wanted to play it safe. We didn’t want him to just do it and just make it awkward afterwards, she wanted him to feel okay with it and tried to normalize it. She met up with him a couple times.
One in public at a park and it was the first time since school where they were by themselves and they just hang out and got some ice cream.
The second time she went to his house (his parents but you got the point) and she asked him if he could help her look for a PC we they hang out. This must have been so thrilling for him to have his crush now in his room with no one else in the house. She played it so well.
As he was sitting on his desk searching on his computer for what she asked for she was standing behind him watching and as she pointed at the screen, her body went over his and when she backed up, she left her boob resting on his shoulder and she could feel his head move against it.
She did small teases like day the whole afternoon and when it was almost time for her to go she sat on his bed as they talked and told him to sit next to her.
She put her hand over his and according to her, he was shaking from nerves. She grabbed his hand and placed it on her inner thigh and told him that he could move it wherever he wanted but only over her clothes.
He didn’t think twice, he slowly moved it around her waist and with the other one he very slowly grabbed her breast.
She enjoyed it and didn’t care about our rule of “No kissing” and started making out with him. She opened her legs and moved his hand back down to between her legs and her leggings were soaking wet. He stopped for a second and she told him that she was “all ready to fuck” and at that exact time, his little sister came home from school.
She told me that they would have stopped right there anyway but not to him. They had a big laugh about him being cockblocked that day so she finally proposed to make it real but with one condition. I had to be there too.
He didn’t care about it.
He said that it would be a little awkward but also he would feel better if her man was there too so it wouldn’t feel “wrong” in a way. She told him all about the cuckolding thing and he knew about and was actually really excited about it, he did say that since it would be his first time that I could be more involved and instead of cuckolding me, we would have a sort of threesome.
This was the best for the three of us and when the day came I couldn’t believe it. I was hard the whole drive to his place. (We set a date where his family would be out of town so no interruptions) As we got in I shook his hand and she kissed him on the cheek.
He had a little friendly chat and when she got up to get started, the whole room got hot.
I got behind her and slowly lifted her dress revealing her lingerie, as he sat in front of us with his pants down. I could see in his boxers how hard he already was. She got in top of him facing him and they started kissing.
He started kissing her neck and then her boobs as he tried to take off the bra and when he did he didn’t let go of her nipples.
I was pretty hard myself and sat next to them and they changed positions and prepared to start fucking. As they did, she was facing me in all fours as he fucked her pussy and I moved my leg so she could suck me at the same time. It was honestly way hotter than I was expecting.
As he got tired I went on his place and I almost came right there but fortunately I managed to hold.
In the end the three of us were sweating and she got on her knees on the floor with me and him standing in front of her as she sucked our dicks one at a time and then tried to fit both in her mouth. He began masturbating to finish and after a few seconds he did and I did right after him. She got cum all over her face and tits and it was one of her hottest looks ever since.
After that day they would still chat but nothing else ever happened, I don’t know why but he was still happy that it happened.
Also me and my wife wanted to slow down on the cuckold thing as we wanted to focus more on ourselves. We got married and years later we got that inch again.
We were adults now on our mid 20s and we felt more comfortable now when it came to find someone else for her to fuck.
We did that pretty often but nowadays it got boring. Like it was always some smug dude acting like he had a golden dick and would make her cum 20 times, just to be average like every other guy. There was a few really good ones that made an impression still to this day but none of them were recurrent bulls. So I remembered the guy we did it first.
She still talked to him often and after that day it was like they had a special friendship. She texted him saying that she was remembering that time and that she missed it and apparently he never stopped thinking about it. That through all these years he always wanted to propose to her something again but since she got married he kinda took that as a closed door.
And she told him that the door might be closed but he still had the key.
Again he didn’t want to intrude on us and she said that they were just talking.
She asked if he still thinks about her he said that even tho he still thinks about her, it’s not like he loved her and was obsessed with her. He tried to have a couple of relationships but none ever lasted and he confessed that ever since he lost his virginity with her that day, he never got to have sex with someone else since.
Maybe because of him being introverted, maybe because of his looks and his weight, he never got lucky in love so when she started talking about it again with him, he was more than willing to do it.
This time we wanted to tease him and not just setting a date to do it. He is a close friend to her at the end of the day so they just hang out with their other friends and just got closer than they used to be.
A few weeks ago her friend group wanted to go out this new sushi place for dinner and they invited me too. I’ve already went out with them a few times and I get along with them just fine. On that day as we sat on the table I was next to her and he was on her other side but on the head of the table so the whole dinner she faced him more and she did me and as the food came they even fooled around by stealing from each others plates. No one else too notice but she’d turn to me and wink in a flirty way. Later on she told me that their feet were against each other the whole time and that he even put his hand on her leg under the table.
He never said that he wanted to be with her alone or set a date, he was just as happy to have her be like that with him on the day-to-day. She also didn’t particularly wanted to have sex with him but she wasn’t against the idea. She told me: “If it happens it happens”.
I was all for that. This way there wasn’t any pressure for anything to happen and it was more thrilling for me for when it does and she surprises me.
The thing is that ever since she started to him again she told the guy that it would have to be a secret so that I wouldn’t find out about it and it would be just a “their thing”. This way he would be more comfortable with her without having me knowing, he could be more himself and just think that is just cheating on me.
A couple days ago he went to our house to help with our PC while I was at work and he was expecting something to happen, specially because my wife was wearing a long shirt pijama with just panties underneath and she was just happy to tease him like that and after he left he texted her that he was super eager to to something the whole time but he respected her as she didn’t do any real signs for him to advance.
So next time she told me that they would actually do something and she wouldn’t tell me when it happens.
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