100% real first-hand account. A bit of background to kind of set the stage. Obviously have to change the names for privacy sake. My wife Ashley and I have been together since college and have been married for 10 years and have kids. We live in an upper middle-class community, I’m a white collar professional and she’s a stay at home mom, pretty normal lives. Our sexual relationship has been strong but like most has its ebbs and flows and we have only been with one another since we’ve been married. A little about Ashley (she’s 5’3, very light complexion, medium length brown hair, 130ish lbs with natural c-cups and a nice full ass. She is a bit conservative when it comes to sex and for years have been trying to coax her out of her shell. I poke and prod her when we have sex to let loose a bit in terms of talking dirty, trying new things, etc. We are pretty open however, based on our close and strong relationship about our sexual pasts. One of her past experiences has always stayed with me. She has explained to me that one of her earliest boyfriends had a rather large cock. She describes it as twice and large and twice as thick as mine and that she would cum constantly from traditional sex. Now, I’m not slouch but I would say I’m average in length and thickness, so if I did the math, this guy must’ve been over 10 inches long. Nevertheless, she has shared stories of her being fucked by him (which she tells me was over 1k times over the course of their relationship). So, aside from sharing some stories, allowing me to take sexy pictures of her, she is pretty modest from a sex perspective. She has never once complained about our sex life and when we do have sex, she definitely looks and sounds like she’s enjoying herself. That said, I haven’t made her cum from penetration, I make her orgasm by rubbing her clit and pussy, which she does enjoy. But, I always think about her telling me about how her early boyfriend would make her cum by fucking her. It truly doesn’t bother me so much as it turns me on for whatever reason. I really don’t identify as a “cuckold” in terms of the humiliation aspect most people identify with that. I simply fantasize sometimes about her fucking her previous boyfriend, no rhyme or reason… So many months back, as we were enjoying some foreplay and I was rubbing her clit, I asked her if she missed her boyfriend’s big cock and whether she wished she could fuck him again. THIS made her cum almost immediately as she said yes over and over again. When we were done she looked at me with this kind of embarrassed face and said “sorry”. I was like Ashley, what do you mean “sorry, what do you have to be sorry about”. She said she was sorry because she thought I would be upset that she came so fast after bringing that up. I confided in her that it actually turned me on seeing her cum so fast and hard while she thought about her old boyfriend fucking her. We both accepted this and kind of moved on… about a week later we were having sex again and during foreplay she asked me to use one of the dildos we have to fuck her a bit. I grabbed it and starting moving it in and out slowly (it’s a decent size, say 8 inches long and 1.5 inches wide). On about the 50th stroke and her really starting to feel it I asked her what she was thinking about as I fucked her with the dildo, she just came flat out with her eyes closed and biting her lip, “Ryan”. Ryan was the name of the previous boyfriend in question. I asked her if she could fuck him right now, would she. Ashley said “YES, please fuck me harder, RYAN, fuck me harder!” She was literally imagining this dude Ryan fucking her while I’m using this dildo. I was very turned on, got back my focus, and fucked her with the dildo until she came. Afterwards, instead of us both being embarrassed, I simply asked her if she wanted to try a new cock, someone maybe bigger, that reminded her of Ryan and would she be open to me watching her get fucked. She was very reluctant at first saying no 100 times. It wasn’t until she truly understood that this wasn’t about me trying to fuck another girl or anything like that, that it was about me truly finding pleasure in HER pleasure. Once she understood and believed that (which again is true) she agreed that she would be into this. From there we talked about who, how, etc. This was kind of nerve racking for the both of us in that we didn’t really know where to start. Do I go online, reddit, craigslist doesn’t exist anymore, what if someone has an std, what if someone finds out, all these thoughts, fears going through our minds. It finally occurred to me that she once referenced my best friend as being “good looking”. I couldn’t remember the context but that didn’t really matter. My best friend Dan and I have known each other for over 20 years and in our high school/college days had had a couple of threesome mfm experiences together, but obviously nothing since then. Like most guy to guy friendships I imagine, we share our sexual exploits, tell stories, and occasionally share dirty pictures of our significant others. But the thought of him fucking my wife has honestly never occurred to me until I remember Ashley’s comment from what must’ve been years ago. So, a few weeks back Dan and I got together at a bar to watch a football game and I took out my phone after having maybe a few too many drinks, showed him some recent pictures of Ashley bent over, her breasts, etc. He made the comment, “Man, you’re a lucky guy, I’m going to jerk off later thinking about that”. He opened the door and I just walked through… I said “you don’t have to jerk off to her, why don’t you just fuck her?”, half ingest… Dan said, “are you sure, we haven’t done anything like that in 15-20 years and your married, she’s your wife”.. I told him it was all good and that Ashley and I were considering this but struggling to find the right person. Dan said he had to think about it and didn’t want to jeopardize our friendship, which also made me second guess bring this up to him. Fast forward to the next weekend we got together to watch another game, we both talked through it and agreed it was all good and that nothing was going to get in the way of our friendship, being as strong as it is. If anything, I felt more comfortable with someone I trust and know than some random guy, so this was a relief. I went home that night and told Ashley that I thought Dan would be a great guy to do this with, I laid out the reasons why and after a while of going back and forth she agreed. She also agreed that she preferred someone that she knew and trusted. A little bit about Dan by the way, he’s about my height 6′”0, about 195lbs and has a pretty large cock. I know this from our escapades in our younger years. He is probably a solid 3.5 inches longer and a bit thicker erect than I am, i remember the couple of girls we fucked together go wild with him. So, acting as kind of an intermediary we all planned how this would go down. With that background, the following is what transpired: Read more »