[MM] I (28M) lost my anal virginity tonight

I have been fantasising about this moment for years, using my fingers or whatever I could find around the house (don’t own any toys unfortunately) to try and get an idea of what I was missing out on. I’ve been on several different sites trying to meet someone to make it happen to no avail. On the rare occasion when I found someone, I’d get scared, my anxiety would flare up and I’d back out at the last minute.

Tonight was different. I arranged a meet on grindr and was at his door an hour later. We went straight to his room where he took his pants off immediately. I was on his cock with my mouth immediately. I’d sucked before but I wasn’t into it like I was tonight. The feeling of it growing in my mouth, knowing this time it was going somewhere else, was really getting me going. I was gagging on it a little too much in my eagerness. Eventually we locked eyes and decided it was time.

I thought it happens only in porn clips [MF]

A bit of context. True story, been together for 10 years, married for 5. We have had some wild sex sessions and definitely try to spice things up in many directions. I do not have a fantasy as such but my fetish is to know that I drove my woman wild. Ideally to the point, when she loses control. That is why I love to lick her and over the years I’ve gotten pretty good at reading her moves.

However, I always try to up my game and last night I was able to do just that.

[MF] Ice Cold Pussy: Sex In The Snow

This particular adventure takes place in the hinterlands of Finland. I know what you’re thinking, hardly the sexiest setting for a story, but hear me out. I was on holiday with my then girlfriend, Ella. Ella was half Swedish, half English and 100% stunning. We had visited her folks, who lived in the Swedish bit of the Artic Circle and drive east to Finland to see the northern lights.

So, there we were in a cabin, which was amongst a little collection of other cabins with a shared sauna, but there was not much else there save for a strip of road, a petrol station and an alcohol shop. Ella and I whittled away the hours by drinking cheap vodka and eating oven pizzas smothered with mayonnaise. These Scandi/Nords are crazy.

It was also the first year of our relationship, so we were still in the honeymoon phase and constantly pressed against each other, hands grasping, tongues flailing and erogenous zones…erogenousing.

Let me bring Ella to mind:

Exhibitionism With [M]y [F]riend

Reuploading a few stories from my old deleted account before I start writing some new ones…

This one’s a little lighter on the kink side of things but is still one of my favorite memories. This was with a girl named Leah.

We had already been on one date where we had ended up back at my place. She was a little vanilla for my tastes, but very enthusiastic. And she had the best head game I think I’ve ever encountered. (It was a total body thing for her, she absolutely devoured my cock.)

After we fucked that first night, we lay staring up at the ceiling having the usual vague, sleepy post-sex conversations. In the course of the evening, I had used a couple restraints on her and a couple toys. Nothing that would qualify as bondage, but enough that she asked me about them afterwards

“So is that, like, your thing? Tying girls up?”

“Yeah, that’s my thing. What’s your thing?”

“I don’t have a thing.” She said, and went quiet. “Have you ever done anything in public?” She asked after a while.

I nodded. She grunted softly and drifted off to sleep.

[MF] A professional massage with a MILF takes a sexy turn (F48/M26)

My dirty secret is that I LOVE GWstories. You wouldn’t expect it. In no way do I present as someone who would be into erotica or reading in general (I kid, I kid). So every so often, I do my part by adding to the community. And today is the day I give thanks with another story from my past. The time I hooked up with my first masseuse. And first redhead. And first MILF. And…you get the idea. A redditor I met loved this story and thought it deserved to be posted, so I hope you enjoy it! Skip ahead to the ***** if you want the juicy stuff. But it’ll be better if you get the setup too. I promise.

I (dude, mid-20s) was living in a big city for the first time. East coast of the US. And it was glorious. Shake Shack like 5 times a week. Drunkenly stumbling home from the bars. Tons of new people to meet. Yep, as you can guess, I was in college. Grad school to be precise.

I 27[M] have sex with a wife 49[F] while her hubby watches, Pt 1 (long)

No one—not my siblings, not my friends, not the people who live in my building—know this about me: I’ve been having sex with wives/moms for 7 years, with their husband’s permission (and often he watches).

I know it sounds strange and kinky (because it is), but I’m a totally normal, hard-working career focused guy living in a major city. I’ve had a fun life of ballgames, hikes, nights out, weekends away and group dinners with friends (except for the whole COVID thing). I was raised with strong morals and have a great relationship with my parents and my siblings and their families. I grew up a nerd and didn’t really become attractive until college so I’m not a chest-beating, braggy kind of guy—I know what it’s like to not be the center of attention. However, now I’m what would be considered traditionally handsome (6’1″, brown hair, blue eyes, fit, fairly athletic). I don’t go to key parties or sex clubs, I don’t identify as being a swinger or in any kind of lifestyle. I date girls my age, but when I’m single I just…enjoy fucking soccer-mom-and-PTA-wives-next-door in their mid-40s to late 50s (though sometimes a little younger or older), often while their husband watches, sometimes on weekday mornings on their dining room table or over the side of their couch. I can’t believe these things happen either.

Consensually Cucked By My Boyfriend [FMF]

Late one night, maybe six months after Calvin and I [started](https://www.reddit.com/r/gonewildstories/comments/qr1usj/against_the_wall_fm/) [dating](https://www.reddit.com/r/gonewildstories/comments/qujedr/against_the_wall_part_2_or_treated_like_the_slut/), we cuddled in bed after another round of furious fucking, idly chatting about some of our deepest, darkest fantasies.

“Your turn,” he whispered.

“Well…” I paused for a beat or two, or three. “I’ve, uh, always wanted to watch you…” I murmured, hesitating, right on the edge.

Calvin smirked, his hand squeezing one of my boobs. “Watch me what? I think you’ve seen me do pretty much anything.”

I nudged his side with my elbow. “No, silly, not this.” I paused again.

“Watch you… fuck another girl.”

This caught Calvin off guard. Hard to do. “A threesome?” he said quizzically.

“No!” I spurted, burying my face in my hands. “It’s okay,” he said quietly, squeezing me against him. “You don’t have to explain.”

Comforted, I turned to face him. “No, really, it’s alright…” A deep breath. “I don’t know… you’re just so powerful, and it would be hot to watch you with someone else. And it would be humiliating – the good kind of humiliating – to have to watch.”

[MF] Family Vacation and my M(36) sister-in-law F(28) PART 2

I want to give special thanks to a special redditor for helping me with my writing ability.

The link to Part One is [here](https://www.reddit.com/r/gonewildstories/comments/qhwvfi/mf_family_vacation_and_my_m36_sisterinlaw_f28/)

Part Two of my family vacation, when my sister-in-law, Tammy, and I took our relationship to another level.

When Tammy and my brother-in-law arrived the next morning, Tammy averted her eyes and looked down at the floor. I had a bit of an issue seeing her as well, since my brain and my cock were having flashbacks of what took place just a little over 12 hours prior.

Tammy’s womanly scent and the sweet taste of her body was still fresh in my mind. I decided to go outside and start the grill. For some reason I became incredibly hungry…. for what, I wasn’t sure of yet.

All the kids were heading to the pool, and Tammy came out to the grill to see if I needed any help.

“I think I have this pretty much under control if you’re asking about the grill, but…”

“Do you think we should talk about last night?” Tammy asked.

“Do you mean regrets? Guilt? or the next time?” I answered.

[MFF] My gf and I had a threesome with our roommate’s friend on New Years

We have been swingers for a few years now and at the time we were just starting out really.

All of my roommates knew of course because it was kind of hard to hide the fact when our gf (our consistent third whom we met on tinder) would come over and disappear into my bedroom with my gf & I for a few hours. Plus our walls were pretty thin…sorry roomies (not sorry).

Anyways we had a New Years party a few years pre-covid (those were the days) and my roommate Diana invited two of her girlfriends over. Both were very cute (believe me I tried to get a 4way to happen that night).

We kind of hit it off with her girlfriend, Emily…and I joked with my gf about having a spontaneous 3way. She said that’s probably not going to happen…anyways…we played games and drank until things started to quiet down and people started calling their ubers. My gf went to bed and said to drop it but I wanted to give it a shot. My gf said she wouldn’t hate it if Emily showed up naked in our room.

[M] Story number one

I’m new to this group and posting all around, so I’m not sure if this is the right place to post this, if it isn’t please let me know. As a background, I am a former Dom that used to write little dirty stories that I started to turn into actual short stories. I have several of them that I’d like to share if there is interest (they get more intense with each story). These are meant primarily for women and have a bit of anal play. This first story has an extended version that was being written into a short story. Please excuse the grammar, as they were written in haste.