gonewildstories Archives — Page 4362 of 5640 — NSFW story

First time anal with a long time girlfriend [MF]

During my final year in college, I met and began dating Jackie. She and I hit it off immediately. We were into the same bands and movies, and shared a similar sense of humor. It also helped that she was adorable. She was 5’4″ 120 lbs. Dark shoulder length hair and hazel eyes. She had some curves too. Only a 34B up top, but her ass was PHAT! I grabbed at it every chance I could, and she would tease me relentlessly with it too.

Once we graduated college, we found jobs in the same area and got an apartment together. Most mornings and weekends were spent lounging around where she would be in a t-shirt and a thong, wiggling her ass around trying to get me riled up. Most times it worked for sure. I was always 100% honest about my desire to fuck her in the ass, but she would always say “I’m sorry, baby. No.”

My first time with anal [MF]

This was almost 30 years ago, with my second girlfriend.

I was 18, girlfriend was 17, almost 18. She lived with her mom, and I was there along with a bunch of her family members for Thanksgiving.

Football on the TV, food laid out, probably a dozen people in the house.

She was frisky, often flashing her boobs, ass, or pussy when we were in public, when nobody was looking. She’d also slide her hand down my pants at any given time. She was always wet, and always horny.

“Follow me!”

We went to the bathroom, where she pulled her shorts off and got on her hands and knees on the bath mat. There’s a dozen people in a room just on the other side of the wall, and this is the only bathroom in the house… but there’s pussy.

I pull my jeans down, get behind her, and slide my dick into her pussy, while grabbing a handful of hair. I reached down and grabbed a tit; she loved them being handled really roughly, and was often bruised. I tried to fuck quietly, but…

“stick it in my ass!” Read more »

My wife (finally) let me cum in her ass [MF]

Over the weekend, the wife and I had a chance to get away from the kids, have a rare date night and stay in a hotel. We were heading to a concert that night and decide to chill out and rest up in the room. While laying down my wife starts initiating by rubbing her pussy on my crotch. She never does this so I take advantage and we have a quickie with her coming on top.

We go to the concert and have a great time. After the concert, we’re back in the hotel. Sexy time starts back up and it is going great. Get the lube out then probing her asshole in the doggy position to gauge her willingness to take my dick. She tells me she can’t handle it like that. I get a bit disappointed since my anal fantasy just got rejected. My wife then let’s me know she wants to be on top. Read more »

An unexpected layover in Dallas [MF]

I’ve seen a few posts on the sub recently questioning how every guy poster bangs some incredible smokeshow girl, how every girl poster finds a dick that’s always the most enormous 27 inch dong they’ve ever seen, and how all posters manage to junk-jackhammer for 2.5 hours straight with seemingly infinite stamina. People come here to share their most incredible and noteworthy experiences, so I don’t see the problem personally. Nevertheless, here’s an event from a couple years back that’s a bit different from most things I’ve read here and should satisfy the sceptics.

A couple hours back, I had found her gonewild post. It was a typical “do u like what u see??” image from a new account – a badly taken close-up of her huge tits squished together, kind of like [this random picture I found on gonewild](https://i.redd.it/u93zwdzrgiuz.jpg). Grainy, bad lighting, unflattering angle, and missing a tag. The girl next door with her flip-phone quality camera generally has no chance on that sub, but that doesn’t mean the photo and girl weren’t both hot. They were. And that made her a good candidate for some fun. Read more »

Truth or Dare Ball – Part II: Thor is Sexy [Group]

[Part I is here.]
(https://www.reddit.com/r/gonewildstories/comments/9jfd47/swapping_at_a_halloween_party_an_intro_to_truth/)

*Names and minor details have been changed for anonymity.*

It was a few days after Halloween, and my wife Michelle and I were anxious to play with our friends Mark and Winn again. We’d had threesomes with women before, but we’d never swapped with another couple. Just the small amount of playing we did with Mark and Winn had been so hot, we were constantly horny just thinking about it. We wanted more. But how, with a willing but reluctant Winn controlling the pace? We went through a bunch of ideas: Spin the bottle? No, that’s fun for a minute but it’s just kissing. Truth or Dare? Maybe, but it’s usually lame. I scoured the internet for hours looking for swinger games to ease in newbies, but there’s nothing good. They progress from “Make out for a minute” to “Anally gangbang the mailman” in like…2 rounds. No thank you. But then Michelle knocked it out of the park. Read more »

The one with the airport stranger [F]

This is it. I said I wanted to be more slutty and I did.

Last weekend I went away for my birthday and I had a great time. On my way back my flight was cancelled all hell broke loose everybody was mad and somehow I was really chill.

I get easily annoyed but this one time I thought even if I screamed at those poor people it’s never going to bring me a new plane any faster so I might just make the most of it.

I comply and my new flight sits me next to this very cute but younger boy :/

Maybe it’s the tiredness or any excuse I can use for myself but I started flirting with him. He lets me put my head on his shoulder because I need to sleep and I get increasingly more turned on.

Next thing I know I tell him about how I always dreamed of fucking a stranger in a plane so we went to the toilets but it was busy and so we decided that if we saw any good spots when we land then it’s meant to be and we should try. Read more »

[F] Hookups and Pies (x-post /r/stupidslutsclub)

*I posted this over there (/r/stupidslutsclub) and they seemed to like it so I figured I’d share here too <3*

A Tinder hookup fucked me raw and came in me without asking, and I loved it.

A few months ago I was in a lull of no sex – it had been a few months actually thanks to life stuff, but I was finally in a place of feeling confident and sexy again so I downloaded Tinder.

I matched with a few folks, and most of the conversations fizzled out pretty quickly.

I got talking to a dude named, we’ll call him “Jeremy”, and we hit it off pretty well. We had the same sense of humor, I sassed him and flirted for a while. It was fun, I felt good. Truthfully, he was fine as fuck at least in his photos so I was definitely turned on for the first time in a while.

Eventually he asked if I wanted to meet, he was only about 30 minutes away. We landed on meeting up after a night at work the next evening. Read more »

Fucking an older woman in Orlando [MF]

Been a while guys, here’s a fun little story from a vacation I took this summer.

A little bit about me: I’m 26 years old, around 6 feet tall and 205 pounds, athletic figure. I have dark brown hair and the same color eyes. Kind of a hairy dude, but so far haven’t heard any complaints about it. I have a couple stories I feel like sharing, and the community on this board seems to be very welcoming to that, so I thought it best to post my experiences here. Hope you enjoy!

I travel quite a bit, and I normally find myself in Orlando pretty often visiting one of the theme parks a couple times a year. I had a week long vacation from work recently and decided to head to Universal resort for a few days. I brought my cousin with me because his girlfriend lived down there and he wanted to see her. Since he was going to be spending time with her I was going to be alone the majority of the trip, which is fine, since it also meant I had a room to myself for the week. So on the second day of the trip, I head on the shuttle bus and go to the Universal Studios theme park. I should mention this was a very last minute trip and I packed like it. I was wearing soccer shorts and a tank top, looking like a real loser. Also rocking a universal fanny pack I bought when we landed since my shorts had no pockets. I was not expecting to get much attention. Read more »

Sarah is [M]y Tinderella [Part 3] [MF]

Gentlemen, and ladies/catfish, sorry for not posting in ages. Life and Sarah have kept me busy recently.

That’s a good way of summarizing the past few months… busy. I’ve had to go out of town for work more than once which sounds cool, but honestly, I’m not a fan of it. It interrupts my schedule of working out and eating right and since I can be pretty introverted, I find myself flicking through the channels alone on weeknights. And by the time I can get home, I have to use the weekends to prepare for the week. It can get grueling and a little lonely.

What’s worse is that one night a week is pretty much all I can spend with Sarah. I took off another Thursday from work which, believe me, we made the most of, but I’m going to stay away from that in the future. Too many of my coworkers are asking nosy questions about if I’m seeing anyone, why I seem to walk with a spring in my step on Thursday morning, et cetera, and I’m not willing to explain the situation with Sarah. Maybe that makes me shallow? Or maybe I’ve internalized a fair bit of slut-shaming? I don’t know. Read more »