About me: I am 27, white guy, about 5’11, 160lbs in weight and most importantly obsessed with the cuckolding lifestyle from a young age. What pushed me to this fetish is the fact that I was always insecure about being skinny, non athletic and with a 5 inch cock. Through the years I have consumed a lot of cuckolding content and it started from a young age when my first girlfriend cheated on me. Then years later my crush chose to get fucked by my friend so, let’s say I was destined to be a cuck from a young age.
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I was never great around women but in college I run into this girl Amanda. 5’8 brunette, amazing body, perky boobs, big round ass with a small waist. I never thought I’d had a chance with her but apparently at the time she was fed up with fuckboys and chose me. Amanda was clearly out of my league and she had a strong type too. She was confident, very independent and took me 3 months of dating before sleeping with her. Fast forward to today we have been together for about 6 years. We have a monogamous relationship, but my cuckold obsession remains. I never mentioned it to her as she never gave me the idea she would want something like that.
I tried to forget about that fantasy as with Amanda it would never happen. She was never interested in flirting with other dudes, she didn’t wear revealing clothes and didn’t liked attention.
Last year I got a new job and there I met a colleague named Luis. Luis was a good looking 6’2 guy, well built and he seemed very smart. I was happy about it as I didn’t have many friends. We talked about football, tech, politics everything so it didn’t took long for Amanda to also meet him. She was happy for me that I had a friend at work with whom I could have fun and we often organised beer nights at the bar.
It was the first time Amanda liked one of my friends and my stupid mind pushed the idea of them sleeping together. I had never seen my girlfriend around other dudes and the was she seemed relaxed with him made me think about it more and more. I wanted to find a way to push the idea to her also but I didn’t knew how. One day while I was out with Luis we were talking about vacations and I started showing him pictures of places I took through the years. In some of those there was also Amanda and when I was showing him some nice beaches we had been through I swiped on some pictures of her in bikini. Of course that was nothing special but it turned me on so much that he was looking at my girlfriend like that.
Another day the three of us planned to go out for some drinks and I decided to skip it last minute telling her I had stomach pain. I told her to go since Luis was already waiting at the bar so she went. I thought giving them some alone time would be a good idea. All evening I watched porn thinking about what they were doing. I texted Luis asking him if he was getting bored and he replied that Amanda is fun and they were having a good time. He told me he would drive her home later which made me even harder.
Days before Valentine as me and Luis were hanging out I asked him if he could come with me to Victoria Secret because I wanted to get Amanda a gift. We took a look around and I asked him what he thought I should get her. Luis suggested this nice red lingerie set and told me she would look great in those. He also suggested some other thongs and bras and the whole experience there was very exiting.
When Valentine’s Day came I showed her the gift and she loved it. I made sure to mention Luis chose them as he was with me when I bought it. She laughed and told me that now my friend would imagine her in those. I smiled and told her maybe he already has.
Amanda loved that set and as she was wearing it and taking some pictures in front of the mirror she told me she would thank him next time as Luis had taste. I jokingly asked her if she was taking the pictures to thank him and she said no because he would take that as an invite. We had a passionate night and the next time we saw him Amanda brought up the topic. She told him he had taste and that it was the perfect size. Luis appreciated her comment and told her he saw many nice sets that she might have liked but that the red one seemed more appropriate for the occasion. He then mentioned another black g string he saw there and told her he thought it could maybe be too much. Amanda replied that the one he got was just perfect and out of nowhere she took out her phone and showed him a couple of pictures she took that night.
I was shocked, I really didn’t expected that move and I saw Luis didn’t neither. He took a good look at the pictures and told her she looked great. The night progressed as usual but in mind I couldn’t stop thinking about what just happened. I didn’t mentioned anything to her but I was hopeful that was a move in the right direction. About a month later we planned a 10 day vacation in Thailand and days before the departure she told me she had to go shopping. She needed some new bikinis, sundresses, shoes and stuff like that. She asked me to join her to the mall and then asked if Luis wanted to come as he had more taste than me in that sort of stuff.
I got so exited, I asked him and he was up for it. We wondered at the mall for a while and I made sure to leave them alone a bit. She was showing him some bikinis there and he was giving his opinion. Luis made a jokes suggestion a really small bikini that barely covered anything, Amanda laughed and told him she would get it just for her to try it out. After she chose like 5 bikinis she went to the dressing room to try them out. Luis went there with her and waited outside. I acted like I was focused on my phone as she wore them one by one showing them to him. Luis was enjoying the view and she looked also very comfortable being that naked in front of him.
The last one was the funny set he chose. She wore them and joked with him saying she was too embarrassed to come out. Luis laughed and approached her and as she opened the door his jaw dropped. She looked so hot in those. Her boobs were popping put and the thong was so small it looked like she wasn’t wearing anything. Luis said she looked amazing in it but that he wasn’t sure she wanted to take the risk and wear them. He the asked her to turn around and my good her ass looked fantastic. The thought was so small and she seemed to liked Luis taking a look at it. She said it was time for her to take them off and he suggested her to take some pictures first.
I decided to distance my self a bit and give them some space. My cock was so hard I couldn’t hide it. Things were progressing so well. We spent another couple of hours there with her buying some dresses and stuff and then she was a nice men store and told Luis she saw a nice shirt and pants combo that looked his style. She suggested him to try it out. They went to the dressing room together and she helped it with buttoning the shirt. She insisted she wanted to buy it for him as he helped her a lot.
When we got home later that afternoon she was much more horny than usual. She wanted to have sex and as I got down on her I could feel her pussy was so wet. I could smell it was wet for a long time and that made me so horny. She apparently loved being semi naked in front of him and for me this was a big win. We departed for Thailand days later and after that vacation things started taking a new turn in our relationship… To be continued.