our first foray into anal, on vacation [MF]

This is a throwaway account. I’ve never posted on here and may never again but I can’t stop thinking about this and needed to tell someone.

This happened a few months ago.

My wife (alias Sam, 38F) and I have been together a long time. We’re in our 30’s, have kids, and our sex life has generally slowed down a lot. When we do hook up it’s typically the same stuff… the same few positions, make each other cum as quickly as possible, go to sleep. We’re both fit and healthy and up for it but life gets in the way.

We also have mismatched libidos. Mine (38M) is sky high, and I’d try almost anything once. I’m also super turned on by anal play, even though I’ve had limited experience with it. Of course we always hear about how guys are obsessed with anal because they watch too much porn and it normalizes it, but it’s more than that for me – I just think anal is really hot, and can feel really really good. And I put my money where my ass is – I’ve experimented on myself plenty and enjoy it quite a lot.

Sam has a lower libido. She can get really turned on and I know how to make her cum really hard, but it takes a lot for her to get in the mood. As for the butt stuff… we’ve tried it here and there before but never went that far with it. We’ve briefly talked about it and she said she was open to it and wanted to try it but it never seems to find its way into the bedroom. I guess the limited amount of time we actually have for sex means we’re keeping it pretty vanilla.

Cue story.

We had an opportunity to go on vacation – no kids, no responsibilities, just a remote cabin in the rural countryside with some friends for a week. We’d been looking forward to this for months and I think we knew that we just needed to get away. We hadn’t had sex at all in the couple months leading up to the trip, so there was definitely a little tension building up.

We both worked hard to get in shape for the trip too. Although I have a bit of a dad bod, I’m a pretty slender guy, standing about 6 feet tall with dark hair. Not overly athletic, but not fat either. Sam is also tall, matching my height with gorgeous blonde hair, fair skin and an athletic build with a flat stomach. She has small but gorgeous b-cups and dresses stylishly always. She’s out of my league actually.

It was our first night on the trip and we had spent the evening with friends drinking wine, eating great food, and taking in the refreshingly clean mountain air. The place had an energy for sure and the wine kept flowing. We’d had a long trip getting there and by 11pm or so everyone was ready to call it a day. By that point Sam and I had developed a nice little buzz and even though we were tired from traveling we were riding high on the vibe.

We got back to our room in the house, a simple but nicely appointed cottage-style room with a comfy queen bed. I had hopped into bed and was already half asleep while Sam did her nightly routine. I was sleepily browsing Reddit and even glanced at some NSFW sites for a minute which got the wheels turning. Sam came out wearing a t-shirt and red laced thong panties and hopped into bed, and without a word from either of us we were at each other – hard.

There was an unspoken nature about it, as if we both realized this needed to happen now. We started making out, massaging each others tongues and aggressively exploring our mouths while our hands wandered. Sam was already softly moaning and I could tell she wanted me more than she has in a long time.

I pulled off her top and caressed her soft b-cups gently and paused just for a second on her nipples with my fingers which made her gasp. She has very sensitive nipples, and I swear I could make her cum just by playing with them. I then quickly moved my hand down her stomach and felt under her panties where her wet pussy was waiting for my touch. The panties were next, so I pulled them down quickly and started to more assertively tease her clit and finger her increasingly wet opening. This was no time for much foreplay though – we were hot and restless and impatient and wanted to get down to brass tacks.

I sat up and positioned myself in between her legs and massaged her breasts for a moment, taking one of her nipples into my mouth and lightly sucking which made her moan and squirm underneath me. She reached for my cock which was still hiding behind my boxer briefs that I hadn’t yet bothered to remove, despite the noticeable wetness developing from the copious precum. This was happening fast.

While she fumbled with the fabric I teased her nipples but after a moment I had to have her. I had to feel that warm, wet, tight pussy around my cock at that moment. I pulled my waistband down and plunged into her in one motion, my briefs still hugging my balls, just allowing my shaft to be available for her. We both groaned with immediate pleasure and gratification. I buried all 8 inches of myself into her warm pussy and she pushed back onto me, wanting more.

Within seconds I began thrusting harder and harder and if not for the wine I probably would have cum in about 10 seconds. Nonetheless she felt amazing and I could barely keep quiet as I moaned how good she felt around my dick. She wrapped her legs around me and then did something unexpected.

“What else would you like to do to me?” she half whispered into my ear. “What did you have in mind?” I replied, breathy as well. “Be creative, but I want to hear you moan like that some more.” My mind started to wander as I considered my options. Sucking on her nipple I pulled out of her, and began to tease her clit and her opening some more, now spread open a bit by my hard thrusts. She was dripping. I went back and forth for a moment, caressing her hood and then sweeping down to her hole, sucking on her nipple until from that alone she was about ready to cum.

On an ordinary night I might have stopped there and suggested another position, but tonight something was different. The energy in the room made us wild. On the last sweep with my fingers I moved down further – past her wet, gaping pussy and gently over her asshole, which was already quite slick from her own juices. She breathed quickly in short bursts, stifling a moan until I inserted my wet, lubricated finger gently but assertively into her very, very tight ass.

In reaction she pushed back against my finger, burying it even further inside, and slowly started bucking, riding my middle finger. If this wasn’t a green light, nothing was. After massaging her that way for a few minutes I slowly introduced a second finger and could feel her start to relax and loosen slightly. I reached for a bottle of lube (which we usually keep handy anyway) and poured it generously into my hand and then stroked my cock, which was now impossibly hard, and dripping precum.

In missionary position still I felt the wetness of her asshole against the tip of my glistening head and pushed into her slowly, patiently. Instinctively she wrapped her arms around me and dug her nails into my back; a silent warning that if I hurt her, she could hurt me too. I breathed hard into her neck, and with my left hand massaged her left breast gently, reminding her that I would go slow. Within seconds I was inside her, filling up her ass with the largest, hardest version of myself ever.

We went slow from there, of course. She is not used to anal play and unlike in porn, I knew I couldn’t just start thrusting. I stayed perfectly still inside her for several minutes, giving her light kisses and waiting for her cue. When she grabbed my ass and pulled me gently in I slowly began to move a little, in and out. Her response was a perfect blend of pleasure and pain, capturing the thrill and pure ecstasy from the moment while bracing against any discomfort. But I could tell she was enjoying it and before too long I was able to slowly move in and out. The feeling of her ass around me was incredible, a tight warm ring of muscle squeezing and milking my engorged cock with every movement, a vice grip that threatened to make me empty my massive load with every pump.

After a few minutes I suggested we try her on top as I’ve read this can be easier for beginners. She rolled onto me and, as if I was in a dream, grabbed my shaft and positioned the head of my cock over her ass and sat down on it. Slowly she eased it in again, and this time it seemed to go easier. After taking a moment to compose herself she started to ride me with her ass, slowly up and down, half whimpering and half moaning with each thrust. From this position I could tease her pussy for the first time and I started playing with her clit, which caused her to bury her face in my neck to stifle her groans. Undoubtedly our neighbors were already aware something was going on.

I reached my hands around and took fistfuls of her cheeks and felt her riding up and down on me, the tightness once again threatening to do me in. With my right hand I slowly traced her ass crack from the top, allowing my fingers to follow it all the way down until I could feel her hole being stretched open, my wet shaft going slowly in and out. With the other hand I reached under from the front and slid two fingers into her pussy which invited them in, and again she could barely contain her vocalizations. Now she was really enjoying this. We continued with that for a little while as she grabbed her vibrator and made herself cum twice while riding my cock with her ass. At this point I could tell she was losing stamina – the intensity, coupled with the orgasms, meant she was ready for me to cum.

We flipped over again with her on her back, except now I lifted her legs up and rested them on my shoulders. With the moonlight coming in through the nearby window I could just barely make out her completely exposed, perfect looking pussy and beneath it her asshole which was just so slightly spread open for me.

I once again positioned myself over it and entered, this time with confidence. I filled her up quickly and for the first time inserted my entire length into her ass. I could feel my pelvis hit hers and she breathed in sharply. By now she was looser, ready for me. I slowly withdrew and thrust in gently, testing the waters. She was now playing with her own pussy and I whispered to her “this feels so amazing, I think I’m going to cum soon”.

With that she changed gears. She stopped touching herself and wrapped her arms and her legs around me. “yes I want you to cum” she told me in between breaths, as she pulled me into her with her legs. I pulled back again and thrust in, a little harder this time. The sensations were indescribable. Again I thrust in, yet harder. And again. Within a minute I was full on fucking her ass, my balls smacking against her cheeks as I entered her completely. She whimpered and moaned in my ear, and while she still felt incredibly tight around my dick I could tell the sensation was becoming familiar and her ass seemed to invite my thrusting, dripping, ready to explode cock deeper into her.

I thrust all the way in, feeling the impending orgasm now rising, and in a few more thrusts there was no turning back. I plowed deeply into her and came harder than I ever have before, pulsing load after load of cum deep into her ass. She dug her nails into my back and I muffled my whimpering moans of ecstasy in her neck as we both spasmed and squirmed against my release.

We’ve not repeated or even talked much about that night ever sense, but I immediately get hard thinking about how hot it was and knowing that when the situation is right, we have this little trick in our back pocket…

Source: reddit.com/r/gonewildstories/comments/xjb9c3/our_first_foray_into_anal_on_vacation_mf