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We have been together for about a year and half. We are closing to our 30’s and we are thinking about we are a good match, settling down and get married, since we loved each other. She is a genuinely nice person. And we have met each other’s family, everything is taking its pace and going well. Honestly, by the looks, she is out of my league, I am luckily to have a woman this beautiful, with a petit yet sexy body and a pair of vixen eyes. She had probably 3 boyfriends before me, and possibly several causal-non-relationship-men on the side, I would give the total number of her body count to 7. Whereas I had only one before her, simply said, she is more experienced than me. She said she’s happy that I am very open-minded that about this imbalance of past sexual history, but actually, that is what turned me on. I used to query her about the details, but she replied very vaguely.
We had sexes regularly and compatibly, and honestly better than my ex. After a while, I started confessing my kinks to her, little by little. At start, I said that I like her looking at me with a disgusted expression when blowing me; and then, a little after, saying that she actually doesn’t like me, and I am merely a fling to her or less, something that she’d throw away or keep for fun, and I would be a fool to get attached to her and etc.. And I loved it, though she did understand, but comply, and maybe, by the end of the day, gained some fun.
Then finally, I reached to my final plot. I confessed to her that I have a fantasy of cuckold. She didn’t reject this idea right away, nor accept it, instead, she pondered on it for a while, rather playfully. Then, a few conversation after, she asked if I really wanted this or it is just an urge, and she proved it rather empirically, we had sex, and then even right in the post-nut clarity, I still wanted this, I had a hard-on just thinking about that. And seeing my erection, she said yes. And in that instance, my heard went from joy to a mixed feeling of excitement and scare.
We agreed on these terms: 1) I won’t be there watching, nor getting any material of sex scenes; we both prefer it what one would call “subtle cuckold”. 2) She would be choosing the bull, and including when and how. 3) Never in the house, or involving anyone from our social life. 4) Always use protection. 5) We both got a chance of aborting, and the other must comply.
We set up a profile on a dating app, some casual infos, pictures that showed her greta physique but no face. It was very easy to find a person suits her, which is loaded with men who want to hook-up. We landed on a guy who is supposedly in his early 20s and is still in college. He is about half a foot taller than me, ripped in a non-intimidating way, tanned, and for the lack of better description, someone whom you’d expect a great sex experience from. And he lived in a close-by city, we are not attached by any common relation, it seemed perfect.
He doesn’t know my existence, for him, she is just another woman looking for a pure physical proposition. He agreed to meet in a bar before moving on anything physical. And they met on one night, I was at home, waiting for her return. It was about 2 hours after she returned. She seemed to be pleased by him, but she talked little about the rendezvous, she asked me whether I really wanted to go through it. And I paused, it must’ve been half a minute, it looked like I was pondering but nothing was really in my mind, and I reached to this image: him fucking her. Simple as that, I got a hard-on, probably harder than I ever had when having sex with her. And we said nothing, she looked at my erection and I looked at her. It went, without any other word.
The date was set to a weekend at a beach hotel by his city when all three of us would be free. And he said that he would come prepared. And for the week before that, we didn’t have any kind of sexual activity. We reserved 2 rooms. She went there before me on the afternoon, since I won’t be free until the Friday night. On my way there, my mind was itching and aching at the same time. And when I got there, the rooms adjacent to hers were all occupied, and my reservation only got me to another way down the hall. I noticed each room has a small compact of 3-piece condoms. I texted and asked how it was going, read and no reply. And upon my arrival, it was already dark, I told her I am here via text, and she wrote back that they were on their way back.
So I lurked by my doorway, which gives a view to the elevator. And maybe 10 or 15 minutes later, the elevator opened. She was wearing her emerald bikini, an opened robe and flip-flops. He was in his boxer swim-pants, hand by her waist. They couldn’t see me from there. And they went inside their room, he pinched her ass on the way in. The night remained silent for the next hour, until I received a photo she uploaded to our shared album: her hand holding a condom filled with, not a spit, but a large gulp of cum, it was thick in a creamy way that seemed would never liquefy, and it was slightly yellowish, which one would have if he didn’t ejaculate for half a month or so.
I texted her, asking how it was, still read and no reply. Honestly, I thought I would be sorry and sad, but nothing, I felt rock-hard. I had to jerk off three times, all looking at that picture. Then, after 3 rolls of masturbations, that was when the regret hit me, what fuck have I done? I really wanted to say the word and quit this, but what is done is done, and I just couldn’t say the word. And I thought I would lost sleep that night, but no, I slept just fine.
It was the thing on the next morning that truly turned the whole thing to the next level, beyond my wildest expectations.
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