I tried cuckholding for the first time with my wife and best friend
Sooo a little back story, me (M29) and my wife (F27) sex life had dried up a little, two kids and two full time jobs it became more of a chore for us, there was no passion. Now we did have sex, almost daily if I’m honest but we both knew we wanted to try more and kept toying with ideas.
We went to a few swingers clubs….it was an experience but we felt a little out of our depth. Like most guys I wanted to try a threesome with two fine ass ladies and my wife wanted to try it with two men. At first I thought I wouldn’t like seeing my wife being fucked by another man but my wife was Persistent, she’d only agree to a threesome with another woman if we first tried it with another man. The idea really didn’t sit right with me so I talked to my best friend Jack (M29)
Now in college, me and Jack were no strangers to a few drunken threesomes with random sorority girls lol, but it felt different, my wife being the random girl in this scenario. We talked it over a few beers and he said “maybe it’s because you’re not comfortable around random naked dudes” and then that’s when it hit me, ask Jack! I jokingly said to him “well why don’t you join us, help us dip our toe into the water” he laughed at first and just replied with a shrugged “dude do you remember how wild we was in college, could you still kiss that mouth once I ruin it” with a stupid grin on his face.
After many more beers and a long ass conversation about it, we came to an agreement. A one time thing, just to help us out, we would never speak about it, wouldn’t let it ruin our relationship and the only rule was no anal or kissing. My wife’s rules not mine. We set a date and I told him we’ll keep it a surprise for my wife and that’s when Jack said “let’s do it now so we don’t have time to think about not doing it”
We headed upstairs, slightly tipsy, and stripped off in the hallway giggling at each other. I walked into our room and told my wife to get undressed, I had a surprise for her, we started kissing on the bed and I told her to get on her knees and keep her eyes closed, I got Jack and invited him into the room and told her to suck on this and guess if it’s me or not. We took it in turns before we both shoved our cocks in her mouth making her gag. Jack started to eat her out and watching her moan to him just lit a spark in me. While she sucked my cock he slid right into her and just destroyed her in every possible, pleasurable way.
We both took it in turns sharing my wife, switching positions before my wife begged Jack to finish inside her, he looked at me for permission and the thought of it, almost made me cum right there. I got off the bed and said “do it” jerking off while he pounded every inch into her. Watching them both moan in pleasure as he finished I just couldn’t get enough. As he pulled out and left a creampie in my wife he said “she needs cleaning up” getting off the bed and heading towards the bathroom. I walked over to my wife, rested each leg onto my shoulders and ate her out, in the moment it just felt so right.
The next few days after our sex life had changed dramatically, every time it felt as if I was reclaiming her back and I couldn’t get enough but I knew I wanted more threesomes with Jack to carry on this feeling.
If you want a part two of our other sessions with Jack let me know ;)
Posted Dec 1, 2025, 8:09 PM UTC