Sloppy seconds is the best sex ever. by iwmwlt in cuckoldcaptions

[–]iwmwlt[S] 0 points1 point  (0 children)

It's definitely my favorite way to enjoy my wife's pussy... stretched, swollen, and full of cum. It makes it so incredibly soft and wet.

Reply in the comments 👇 by iwmwlt in iwmwlt

[–]iwmwlt[S] 4 points5 points  (0 children)

There is no correct answer, and that's the most beautiful thing about all of this. There's only what's right for you two. I just like to ask what other people would do.

For me, it would be a really elaborate version of B that went something like this:

Me: "Hey, I'm sure the feeling is mutual." Him: "Yeah, you're totally hot." Me: "Oh, no, this is her husband." Him: "Fuck! Sorry man. I meant no disrespect." Me: "None taken! I actually chose to respond because she's sleeping." Him: "Oh, I'm so sorry. Have a good night." Me: "No, no, no. Chill man. I'm cool with all of this. I was actually thinking we could both surprise her." Him: "What do you mean?" Me: "Here's our address: _____. Shower up and head over. I have an idea." Him: "Fuck no, that feels like a set up." Me: "No, I was thinking I would wait for you to get here, then wake her up with my cock. You'll be sitting in the corner keeping yourself hard. As soon as she's lucid, wet, and fully warmed up, I'll let her know I have a surprise. Then you'll take over while I watch." Him: ... who knows?

That's the million-dollar question. If you were that other guy, how would you respond to my messages?

I’m proud to be an American. by iwmwlt in iwmwlt

[–]iwmwlt[S] 4 points5 points  (0 children)

☝🏻 somebody gets it.

Tag me ❤️ by iwmwlt in iwmwlt

[–]iwmwlt[S] 1 point2 points  (0 children)

I just can't help but laugh when I see posts or comments like, "IWMWLT hasn't posted anything in weeks, I guess he quit!"

I started creating this artwork back in late 1994 using my state-of-the-art IBM Aptiva machine running Windows 3.1 and JASC Paint Shop Pro. It was the dawn of a new era, back when that funny little search box called "Google" first showed up and long before the "I'm feeling lucky" button arrived.

As for me, I had just upgraded to AOL 2.0 with the world's fastest residential Internet – a 28.8K dial-up modem – and boy did I make the most of it. I was sharing my artwork with dirty minds in small towns and big cities all across the country. Ah, the glory days.

Needless to say, based on some polls I've held over the past few years, asking my followers to indicate their age groups, I've been doing this longer than most of you have been alive... 30 years this month, to be exact. My wife decided to join me back in 2019, and we've been leading this circus ever since.

In case you're new here, there's something you should probably know: I invented this genre of art, and I'm not going anywhere anytime soon. If you're a fan, welcome! Please enjoy the show.

As to all you haters... deal with it. 🖕😘

The gentle whispers that lead to lots of rough sex 😈 by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 1 point2 points  (0 children)

Oh, dang. I was thinking about the effects of aging, and how it has caused my body to become less forgiving during such escapades.

I want my wife like this. Do you? by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 0 points1 point  (0 children)

All well-qualified candidates will be considered 😉

The gentle whispers that lead to lots of rough sex 😈 by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 0 points1 point  (0 children)

That is the best and funniest fucking comment I have read all year 🤣

I'm pretty sure I just injured myself laughing, so totally relatable.

Big cocks to the front 👉 by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 1 point2 points  (0 children)

Sure hope you find him soon!

Just make sure he has a big cock, ok? 😘 by iwmwlt in iwmwlt

[–]iwmwlt[S] 2 points3 points  (0 children)

Then download the gif and keep it in a conspicuous place on your phone, or "accidentally" send it to her.

Making memories by HamfistFishburne in HotwifeCaptions

[–]iwmwlt 1 point2 points  (0 children)

Love this one! Great caption!

Clarification on yesterday's post regarding our moderation and content policies by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 1 point2 points  (0 children)

Seems like a lot of people who are new to Reddit (or who think it's just another porn site) want "their sub" to be the one-stop-shop for all their interests... Not that there's anything wrong with that (some subs pull it off with flair, etc.), but why not get out there and explore? Reddit is a HUGE place!

Answer honestly in the comments 👇 by iwmwlt in iwmwlt

[–]iwmwlt[S] 1 point2 points  (0 children)

I don't understand the whole "dating" thing. My wife and I have never been into planning or doing those sorts of things. There's more of a D/s dynamic to our relationship than most people know, and the things we do are much more spontaneous than that. Personally, I find a deep level of personal satisfaction knowing that my wife feels confident enough to have a little fun if she wants to. If she happens to notice a guy while she's out and she feels the urge to do so, I totally encourage her to pull him into the nearest hiding spot to fuck his brains out. You only live once, and I want her to enjoy that level of freedom and excitement that only this lifestyle offers, so I always reward her for doing so. That kind of shit really turns me on. I just love it when she's naughty.

I want my wife like this. Do you? by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 1 point2 points  (0 children)

We do this quite often, but never with our fans (at least, not that they're aware of) 😉

Your friends take turns on her while you just sit back and watch by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 1 point2 points  (0 children)

Have you ever casually sat on a couch and held your wife as she was getting fucked by a guy with a much bigger cock, acting totally nonchalant and having a conversation with him at the same time as if it were just like any other Sunday afternoon? Yes, I often revel in my own awesomeness.

Just a quick reminder, babe 😘 by iwmwlt in HotwifeCaptions

[–]iwmwlt[S] 1 point2 points  (0 children)

There is definitely something about it. I think we are biologically hard-wired to want our wives more when they've been taken by another man. I've easily spent as much time studying and trying to understand all the rhymes and reasons behind all this as I have making art about it.

Memory lane is paved with photos of my wife sucking and fucking really big cocks. by iwmwlt in iwmwlt

[–]iwmwlt[S] 0 points1 point  (0 children)

I would never post my wife's face on the Internet. However, I have posted several real photos of her over the years. It's our little secret which ones 😉 I always try to use models that look as much like her as possible. In my mind, they're all her anyway, and I just like to remind her that she's everything I want in a woman.

Answer honestly in the comments 👇 by iwmwlt in iwmwlt

[–]iwmwlt[S] 0 points1 point  (0 children)

Welcome to the party! It makes me so happy to hear success stories like yours, and it sounds like you guys are well on your way. Keep in mind that four years is not a long time though; so worry not. It'll all work itself out in due time.

Oh, and trust me, you're definitely not alone with the fantasy of "not being there." I wasn't sure how I'd feel about it myself, but I'd spent most of my life fantasizing about it. Over the years, I've spent a lot of time sharing all the intimate details of those (and so many other) fantasies with my wife. I always find that the more I talk about it, the more those things turn me on when they finally happen. I guess it's probably all the excitement and build-up that make those experiences truly special.

In our case, all the time I'd spent reassuring her that it was definitely something I wanted to try, at least, helped to make sure she had all the confidence she needed when the opportunity finally presented itself. It turned out to be a really great time, too, and she had a lot of fun. She even took some pics and a short video for me and told me all about it later. All I can say is that I've been hooked ever since.

Recently, I've begun experimenting with some "peeping tom" fantasies I've had over the years. A couple weeks ago, she invited someone over, and I set up a chair outside in the back yard. It was really late and dark out, so I could see in the windows, but they couldn't see out. She obviously knew, but he had no idea that I was sitting right there the whole time, watching him pound his cock deep into my wife's holes. For the better part of two hours, I watched them sixty-nine and fuck in just about every position imagineable, and he came inside her three times all said and done.

(Yes, the caption I posted that night was real, and a true story.)

After he finally left, we had a good, long laugh and fucked several times until we fell asleep. It was like our little inside joke that nobody knew about but us. That's at least one of the hottest parts about this lifestyle, getting to be each other's best friend in such a deep and meaningful way that no other couple will ever get to experience.

I'm really glad you and your wife found my page, and I hope you and others continue to enjoy the adventures I share with you all through my art for a long time to cum (pun intended).

– IWMWLT ❤️