Hello! I just want to introduce myself and start writing out the story of how my GF and I are progressing into exploring cuckolding. I am 27 and she is 24, and we have been together for about 5 years now. I am your typically “type A” personality who has been sexually submissive for as long as I can remember, and because of this, we have had somewhat of a femdom bedroom where my GF is dominant over me.
This eventually led to me bringing up cuckolding to her a few years ago, and to my surprise, she was more intrigued than negatively shocked by it. Since then, we have incorporated cuckolding as a theme in our sex life, though we have not gone all the way with it yet. She likes to tease me about guys she finds attractive, and we have slowly been increasing the discussion to the point where we would like to try it at some point soon. We generally aren’t comfortable playing locally as we want to keep this private, so a lot of our “plans” are based on us taking vacations and finding opportunities to bring it to reality. So that is a brief introduction, and am welcome to questions if anyone has any.
Now, I’d like to share the experience that we/she had that pushed us as the furthest down this road. For an idea of what she looks like, feel free to PM me.
As for the story… Back a few months ago, one of my GFs best friends was switching jobs and asked my GF and a couple of other girls to go on a girls trip to the Caribbean. It was a group of 6-7 girls and they went for just under a week. My GF and I didn’t have a chat beforehand about anything cuckold related, but in the back of my mind, I was excited about her going to a beach resort with just the girls and imagining the looks and flirting she would receive from guys.
It’s been a few months, so some of my recollection will be vague but if anyone has questions about more details, feel free to ask! On the first day, we were messaging each other and she was giving me updates on how the trip was and just normal mundane conversations. She then randomly sent me a short video of her girls group sitting on beach beds/tables with a group of guys, and in particular sent me a video of her taking a shot with another guy, with his arm around her neck hugging her. She had done that unprovoked and instantly turned me on knowing she was wanting to tease me while she was gone. In the video, she was in a pretty skimpy bikini – not super skimpy, but enough that she was showing a fair bit of cleavage and a bottom that showed the creases of her ass quite clearly. Seeing that definitely sent my head spinning.
After that, we chatted a bit more and she acknowledged that she was teasing me and that she’d continue doing that until I told her it was too much. Naturally, I told her nothing would be too much and that she should keep going. She semi warned me after I said that, but I told her to have fun. That group of guys became her groups main friends for the trip, but not much happened with them. A few of them hit on my GF and she told them she had a BF and then they would back off.
I forget which day in, but her group of friends befriended another group of guys. This was a group of black guys and this is where most of the fun began. So similarly to the first group, one particular guy took a real liking to my GF and began to flirt and hit on her hard. She brought up the fact that she had a BF to him as well, but he didn’t really back down after hearing that.
This is typically when my GF would shut a guy down hard, or just completely stop engaging with them.. but she chose not to for this guy. She found him extremely hot as well (tall, black, great body) and while she didn’t engage back with the flirting too much, she would let him be around her on the beach, he would compliment her and she would smile at him and dance around him on the beach in her bikini. He would get more confident and grab her by the waist to dance a bit, and start ramping up his compliments by talking directly about her body and particularly her ass. She would lightly shoot him down, but would keep teasing him and giving him signals to keep going.
The entire few days that this was happening she continued to tease me via texts and keep me posted. It goes without saying that I was mesmerized by these messages, and probably more turned on than I have ever been. She told me that she found him hot and that she was enjoying his attention. She told me that she enjoyed feeling free on this vacation and that she would like to continue to explore this and push our boundaries.
She was really good at keeping me informed and kept letting me know that she would only push this if I felt comfortable and that I could shut it down at any point. I expressed to her all of the feelings of arousal, humiliation and submission I felt reading her updates, and that I trust her entirely and that I trust her entirely and that she could explore this to whatever level she felt comfortable with.
So this went on for a few days between them two. He would get more and more confident making moves on her, and her responses back became more and more open. It definitely gave off a vibe that he was breaking her down and getting her prepped to “cheat” on me with him, which I thought was super hot. He must’ve felt very confident and powerful seeing her break down her wall and allow him to make advances on her despite her saying she has a BF. The power dynamic of that was incredibly arousing for me. Plus him being black and ripped made it even more so.
On the final night of the trip, my GFs group of friends went to a restaurant/club for the night with that group of black guys. My GF told me that that guy didn’t leave her side the entire night. They did shots together, she would have his arm around him when they were talking into each other’s ears. He would hold her by the waist, he would dance with her, she would spin around him and tease him with her body. My GF explicitly told me that they got along really really well and that there was so much sexual tension between the two of them.
Hearing that made my heart and stomach drop, while also making me hard as a rock. I guess this is what cuckold angst actually feels like, and I am getting those feelings just retelling this story. This went on the entire night between them, to a point where one of the guys from the initial group they met came up to her and asked her if she was okay, and if she needed to be “saved” from the black guy. She quickly turned that down.
At the end of the night, the club was closing around 2am but they didn’t want the night to end. The group of black guys invites my girls group back to their place to continue partying which the girls agrees to. Back at their place, while they were all together in the same room, each girl was talking to one guy and so they were in their own little bubbles. Again, my GF described the sexual tension between her and her black guy as being even higher than before. They were chatting together the entire time. He would dance with her, they did more shots, his hand was either around her shoulders or her waist the entire time. My GF was very touchy with him as well to a point where he told her that she can’t keep her hands off of him to which she just smiled.
He touched and grabbed her ass multiple times and they were basically all over each other without anything extreme happening. Btw, this part I wasn’t getting updates on live. She retold me this all after, I just knew they were going back to their place so I was dying inside of anticipation. The girls were at their place until about 5am and the peak their encounter happened just before that. So as they were together and pushing boundaries, he told her multiple times that he needed to be separated from her otherwise he wouldn’t be able to contain himself. He playfully left, and when he came back a few minutes later, it looked like he wanted to whisper something in her ear, so she turned to him and he stuck out his tongue and kissed and licked her earlobe.
Omg. He did that for a few seconds before she pulled back and playfully danced away. He followed that up by coming back to her, and thinking that he was going to go for her ear again, she tilted her ear away and he ended up grabbing her ass and went to kiss and lick her neck. She then explicitly told me that she intentionally raised her head so he would have more access to her neck and she let him do that for 5-10 seconds before pulling away. Wow. When she told me this I felt every emotion imaginable.
She told me that in that moment she was so turned on and wet, but she was scared her friends would see what was happening and so she fully pulled back and went to sit with her friends. He soon joined as well, and sat beside my GF with one arm around her waist and his other arm on her bare thigh. My GF expressed how in that moment, she wished that her girl friends were not there so that she could let him do what he wanted with her and so that she could have sex with him. But with her girls there, she was scared of being caught or have them thinking she was cheating/thinking less of me.. so she didn’t let it escalate anymore. The night ended soon after and they went home around 5-6am and she flew back home the following day.
Retelling this story brought be back to those thoughts, so apologies if some parts of that story were incoherent or not well written.
Source: reddit.com/r/gonewildstories/comments/xy0i5k/24_f_gf_exploring_cuckolding_for_first_time