If you’ve followed my posts and occasional stories, you probably already know that over the last 5-6 years, I’ve learned that a little ass play can be a fun addition to any relationship and in the right circumstances a tongue or a little pressure back there feels as good as anything. That being said, besides a couple of drunken attempts (which didn’t end up with anything in my ass) and one session of just the tip in my backdoor, I’ve never had anal. And I’m perfectly ok with that.

A little bit about us before I dive in. We’re early 40s, married very happily for a little over 10 years, we have a few kids who we adore, and about 6 years ago we started taking lots of pics and videos in (and out of) the bedroom to post on here. We do it because it’s fun. It’s hot for both of us to make the content and we love having a little secret that our real life friends have no idea about. I’ve often wondered whether any neighbors or friends of ours have seen our posts but have no idea it’s us.

Ok, so today’s story… (along with a handful of pics and a video from the experience)

My husband and I just got back from a little long weekend together. If you have kids on your own, you know it can be tough to relax and let loose when they are anywhere nearby, so when we go away just the two of us, we tend to experiment a little. Good combination of lack of stress and being somewhere where no one knows us leads to open minds.

Our first afternoon in town, my husband dropped a little bomb on me. Erotic/tantric massage is legal where we are and he had booked us a couples tantric massage for that evening IF I was up for it. This was a tough one. I was legitimately turned on by the thought of it, but I can’t quite get past the idea of paying for anything sex related. Honestly, I wouldn’t be able to stop thinking that our masseuses don’t get to choose to touch us like that, they just have to because it’s their job, and that was just too big of a turn off for me. So, I told him we’d need to pass on that idea but that this evening we could still have plenty of fun. Big smile from him and not another word about it.

We checked into our room a bit later. Absolutely gorgeous. A private balcony overlooking the water. We like to take advantage of balconies so he immediately asked me to pose for him. Having already had such a sexy convo earlier, I saw no reason to wait. I went out onto the balcony, leaned over a chair and slowly slipped my lulu pants and green thong down to the floor. (https://i.redgifs.com/i/definitivebigheartedworm.jpg) I could hear him moving around behind me, taking some photos from further away and then getting closer to my ass and pussy peeking out from behind. (https://i.redgifs.com/i/usedexpensivexerus.jpg)

I was soaked. Feeling so exposed to him, the camera and the chance that someone from the ground looking carefully could easily tell what was happening. A moment later I felt him slip right up behind me, slide my legs a little further apart and bring his tongue to my clit. He slid from my clit slowly up through my literally dripping lips and then gently over my asshole. I exhaled deeply. It just feels so relaxing when he does it right.

His tongue stayed right there, gently flicking over that very tender spot. I leaned further over the chair and spread my legs a little more. His tongue moved faster and faster and his thumb reached up and under to my clit, rubbing it in circles and taking my breath away. I felt the thumb sink in, curling forward to move up to my g-spot, and at the same time, he used it tongue to add more pressure to my ass, slipping the tip of it into that ring. Deeeeeep breath. “Ugh, wow, this is intense.”

He kept that up for a couple of mins. I tried to keep my moans to a minimum considering I had no idea who was down on the ground and whether the neighboring balconies had their doors open and people could hear us in their rooms. The pressure of having both his thumb and tongue inside me from two sides was awesome. Not the first time he’s done this but this may have been the best.

“Did you bring the butt plug?” Never thought those words would come out of my mouth. He’s been trying to get me to try it for years but honestly, it’s just scared me. His eyes went wide and within half a second, I was empty and he was moving towards his suitcase.

“Slow down dude! I’m open to trying it, but you need to listen to me. If I say that’s enough, you damn well better listen.” He readily agreed. No surprise there.

“How should we do this?” I asked. I had assumed we’d try with me on my hands and knees and ass up in the air, but he suggested I lay on my back, legs spread wide. With the butt plug laying next to me, he lowered is face back down into my crotch, starting with the clit and slowly, gently working his way up and down through my lips. At the same time, his thumb, with a generous amount of lube on it, began to rub my asshole. Very gently, just working it over and over with a little pressure to get me relaxed and used to the feeling.

I couldn’t tell you if it was 5 or 25 mins. I just zoned out, enjoying the feeling, slowly working up towards an orgasm from his tongue and thumb but neither of us were in a rush to get there. After a bit, I realized his thumb was slipping in and out of my ass, not far in there, but it wasn’t uncomfortable at all. “Alright, babe, I think I’m ready to try this. Grab the plug and let’s see how it goes.”

He squirted LOTS of lube onto his fingers. Covering the plug with it and rubbing the rest into my very exposed asshole, with my legs lifted up and back about as far as I can. The first touch of the plug to my ass felt chilly. Whew, kind of a shocker. It warmed though as he moved it around against my hole and slowly started to add a little more pressure. My husband had told me once that I should push out while he tried to push in, but nothing was happening. He added more and more pressure but my butthole wouldn’t budge. That plug wasn’t getting any closer to being inside me. And the pressure without it opening didn’t feel great either.

“How’re you doing cutie? I’m not sure this is happening? Want me to take a break?”

Damnit, I was finally up for this and while I had the courage, I was going to do it. “Here, let me see if I can get it in.” He handed me the top of the plug. I repositioned it a little and slowly started working it in. Not sure if it was the angle or just me being nervous when he was doing it, but I could feel it start to make progress.

I lifted my legs back just a little more and started to rub myself while I kept putting pressure on the plug. (https://i.redgifs.com/i/triflingmediocrehoopoe.jpg) I could feel my ass stretching around it. It’s not awesome, but it isn’t painful either. I looked up and my husband is in shock, just staring (and filming) while I kept sliding it in a tiny bit at a time. It definitely felt a little better if I wiggled it each time I pushed a little more.

“Oh man, this is stretching me…”

All of a sudden… pop. The pressure changed drastically. I felt so full (I guess that’s the right way to describe it… .)

I just looked wide-eyed at my husband. Not sure I even said anything but in my head, all I could think about was, “it’s in, it’s in.” (https://www.redgifs.com/watch/aptimperturbablecrossbill)

I watched a grin grow on his face and his dick looked possibly harder than I’ve ever seen him. “So… what do we do now?” he asked as he started to rub around my asshole and move the plug ever so slightly.

So, quick backstory… I’m not a huge porn watcher. I don’t mind it at all, but I don’t pull it up when I’m alone and in the mood. That being said, videos of double penetration have always intrigued me. So, of course, since the back is already filled, I responded with, “wanna try and fuck with this thing in?”

After a couple of pics to document the moment for you all, (https://i.redgifs.com/i/niceotherdarwinsfox.jpg) he slid his hips up to my thighs, pulled back again, and started to run the tip of his dick back and forth between my clit and my opening. Since he’s a decent size I like to be the one to guide him in. I reached down, grabbed his shaft and placed his tip up against me. I shifted forward a bit and tried to pull him into me. No dice. I definitely felt super full already but wanted him inside me, now. I kept lining him up, he’d push and I’d shift my hips up into him, but damn, it wouldn’t fit. That thing in my ass was blocking him!

Maybe I just needed to relax a little considering this is the first time I’ve had anything significant in my butt. “Hey, go down on me for a few mins. Maybe that will help.”

That man gave me some of the most relaxing and pleasurable oral I’ve ever had. He took his time. He’d focus on everywhere just around the clit without touching it. He’d play with the hood of my clit, but not drop down a tiny bit. When he finally pulled my clit into his mouth, started sucking and flicking his tongue over it, I came. Really hard. I was panting, I was moaning. I didn’t give a fuck what the neighbors in the hotel might think. God, one of the best I’ve ever had.

As I came down a little, I still felt like I needed to fuck. I love a clit orgasm but if I can get there from penetration, that’s so much deeper. To help loosen me up a bit, he tried to slip a finger inside me. The plug was literally blocking him from that too. It took him almost a minute to get his pointer finger inside my vag. And even that was too much for me. It hurt my vag more than my ass. I literally had never thought that having even a small butt plug in my ass would keep me from being able to get anything in my vag.

Ok, last try. I flipped over into doggy - which has been my fav since I lost my virginity the summer before my junior year of college. (https://i.redgifs.com/i/ickypassionatelouse.jpg) Nope, not even close. He was still rock hard and couldn’t even get the tip in. “Fuck it. I’m taking this thing out and we’re fucking.”

It probably took me 15 secs or so to slowly work it out of me. When it slipped out, I felt a sense of relief but also missed a little of the fullness it gave me.

As you can imagine, I put my ass back up in the air, ready to fuck, and instead of slamming into me, he spread my ass and started taking pics. (https://i.redgifs.com/i/sarcasticexperiencedamericancrayfish.jpg) “Really?? I’m waiting and ready to go and you’re gonna stop to take pics???” Luckily, a few pics later and his reassurance that my asshole looked exactly as it always does, he knelt behind me and slipped inside. He felt even harder than normal and we fucked loudly until he came in me.

My thoughts on using a butt-plug? Not an every day thing for me but would def try again from time to time to see if sex with it is possible. 7/10

My husband on the other hand? He woke up the next morning and immediately asked, “So do you think we could try just the tip anal tonight?”