gonewildstories Archives — Page 3439 of 5640 — NSFW story

Late night random drunken sex with a much younger man. The second day of my cruise. [MF]

This is the second day of a break up celebration cruise, a singles cruise, for myself and best friend Stephanie. We are both 48, I’m newly divorced, she’s just split from her husband. I’m a blonde taller, chesty, I shave myself bald now that i’m single. She’s thicker, brunette, sassy.

We get wild this night. We start off at dinner with lots of drinks and eating steak.

Then we go to a bar in our ship… the one open latest. We have so much fun talking about old times and laughing. We shut the place down. We are so drunk, but now what?

We spot 3 young men on the deck, mid 20s. They look like slim shady’s. Rap fans. All 3 white, and skinny. We ask them for cigarettes. And honestly it’s a blur. We laugh, and invite them back to our place. The one really skinny one is the leader, talker, he’s got glasses. The other two IDK, i dont remember much.

I ask skinny if he wants to check out our private deck. We go out and the curtain closes behind us. Privacy. I hope the other two or atleast one try to have fun with Stephanie, that chicken. Read more »

[MF] Lost 2 football bets

Posted this story a while ago, but thought I’d share it again for those that might have missed it.

Week 16 of the football season I lost a football wager with a buddy (Dallas/Philly). The stakes were nude pics of our wives, and unfortunately I lost. He got to see all the nudes of my wife, and I didn’t get anything. I also had to share the nude pics of her on the dallas and philly r4r’s.

Guess he liked what he saw, because he said he wanted to try and get with her. Meanwhile, I still wanted to see the pics of his wife, so I figured we’d make another bet, and one I was sure I was going to win. If I won, I got to see the pics. If he won, I had to arrange it so I took the kids away for a day with the wife home alone, and let him know so he can pop by and try it out. I got to pick the game, so of course I went with the sure bet of Baltimore beating the Titans in the playoffs. That didn’t turn out so well. Read more »

I [F19] won the race but lost my virginity [FM]

Hey there~!

I’m an asian-american from a quiet little town in the states, but who goes “home” to a large, bustling capital city in Asia every so often. While abroad, I love to immerse myself in their local motorcycle and legal street-racing scene. There’s one long stretch of highway in particular leading away from the city into the countryside that became a haven for hot rods and thrill seekers such as myself.

It was around 10PM on a Tuesday night, and my cousins (all older boys) dragged me out for a night on the town with them. I’m the youngest in the family, and the only girl. Growing up, I had more typically masculine interests, and I was just now finding out how much that turned on men.

I started riding motorcycles when I started high school, so by this time, I’d been riding for around four years. While I wasn’t able to bring my bike with me overseas, one of my cousins had a nice semi-automatic underbone that was pretty comfortable.

*”Ey, look. It’s the fresh grad!”* I heard someone call out. My cheeks pinked. Read more »

I [F]ucked a virgin at a church retreat the summer after I finished high school

I’d just finished high school. My father was recently remarried to a holy roller who had convinced him to go to her church’s annual summer retreat. He wanted me to go because I lived with my mom and didn’t spend much time with his new instant family.

I wasn’t happy about going, but I wasn’t planning to misbehave. It just sort of happened that way. I saw this lanky nerd trying to get laid and I decided to give him just what he wanted. Turns out he was a virgin. My very first. I’d only been fucked by jocks who weren’t always good at sex, but they’d at least done it a few times.

Poor Larry blew his first load surprisingly quickly.

It seems [my curves](https://www.reddit.com/user/NoStereotypeIncluded/comments/f5inyp/my_curves/?utm_source=share&utm_medium=ios_app&utm_name=iossmf) were more than he could handle.

So I let him eat my pussy for a bit until he was ready to fuck and then I gave him his first piece of pussy. Needless to say, he was grateful.

[You can check my profile for all the explicit details.](https://www.reddit.com/user/NoStereotypeIncluded/comments/fbbtfo/i_fucked_a_virgin_at_church_camp/?utm_source=share&utm_medium=web2x)

Not the typical GW story, but I need to get this out [FM] (long) (Part 2)

[Here is Part 1](https://www.reddit.com/r/gonewildstories/comments/fbe7v2/not_the_typical_gw_story_but_i_need_to_get_this/)

Apologies for the formatting. On mobile.

To recap. I’m about to travel halfway across the world. Before I do so, I spend the last couple of couple days in the country with this man. It feels substantial because this is my first trip since admitting the depth of my feelings to him just a handful of weeks ago. We have a D/s dynamic.

So say departure is Saturday, then this would be Friday. I am in the office this day for some meetings I couldn’t take from home. I meet him after work. He’s at a bar in my neighborhood already, so I meet him there. This is a special occurrence. We tried to keep our interactions to the bedroom. It is starting to extend outside of that. It’s complicated. I ramble to him about my day. I finally manage to ask him about his. I’m happy he’s next to me. Seeing him two days in a row is a treat. I start to ask about food, laying out some options. My cupboards are a bit scarce as I am about to be out of town for weeks. He mentions an Italian place around the corner, one I’ve been meaning to try. Internally, I’m lighting up a bit. I don’t know if he can tell. This is shaping up to be a date. We don’t really do dates. I typically don’t really like dates. Man did it end up being the best date. Conversation easy. Silence tension building, not uncomfortable. And the pasta was great. I’m particular about eating pasta out. So is he. We leave to walk back to my apartment. Read more »

Not the typical GW story, but I need to get this out [FM] (long) (Part 1)

So this doesn’t exactly feel like the right place for this kind of story, but it’s the closest I can come up with. I need to get this all down and off my chest. I tried to go full slut and just give the juicy scandalous details. It felt too insincere. Yes, even to total anonymous strangers.

I want to give some background. I’ll do the whole all caps “this is the sex part” down below. So. I’ve never been a girlfriend. I’ve never felt like I’m the girlfriend type. That used to be in an ugly duckling syndrome way. I was a late bloomer. Now I can do quite alright for myself if I want to. I get told I look like an actress that is generally deemed attractive by society. It is mortifying every time. Outside of that, I’m quite confident and self assured. Career woman! Etc. Currently I’m not the girlfriend type, because beyond being career minded, I’m that fun broken girl trope. Refreshing! I shun away feelings (well feelings that aren’t rage! Boldness! I’m your standard fiery girl, down to the red hair. I warned you – trope. I am not a manic pixie dream girl. But. I wouldn’t exactly say I’m original in my issues, either.) You’ll never guess what happened next! I fell in love with a man that does more for me than I ever thought possible. I’m still not a girlfriend, but in his arms, I am happy. This is the story about seeing him right before I took a trip halfway across the world. My first time traveling since telling him I’m in love. Read more »

[MFF] [M23] Very short but good style story about young cuckold with a throphy gf addicted to B.D.E. [F31] [Mwhatevz]

someone’s gf is waiting on a wintery metro station, she is anxious inside yet super confident on outside, she is about to take the biggest cock of her life, you would tell that girl as sassy spoiled like as her had all kind of top cocks but NO,

she has her legs spread confidently , is in full winter clothes, otherwise would be smoking cigs but she is healthy bitch (she wants as many top potential rich alphas as possible every since her girly bitchy bf proposed this “lifestlye”, she let herself lazy in that half a year long normie relationship but she thought that ppl should settle down a bit in early 30s.

Now she wants back in the fucking game, so she chews on a apple just to do something. Her boyfriend is ONLY 4.5 inches and thinnish and curved and doesn’t last long. This fetlife guy has 8.5 which is a double so he should at least last double time than her bf

so like this kind of girl is totally ready to travel for 30 mintues during winterstorm for 7 minutes of sex AT MINIMUM. Read more »

I 48F try to get a lady happy ending massage from a young Hispanic masseuse, on a cruise but get shot down…so sad [MF]

This is kind of a tease story, no cumming. As mentioned in my previous story, I was a newly divorced 48 year old lady. I had my first cougar cub experience in my previous story, and kind of developed a taste for it, and started craving it.

My best friend since elementary school Stephanie, also 48, just broke up with her husband. She’s getting out of a verbal and emotional abusive relationship. Her mother and kind of like a second mother to me, pulled me aside privately. She has offered to give me $$$ to take Stephanie on an all expenses paid singles cruise ASAP, like in couples days. Steph’s mom knows i’m single now, and can have a good time with a couple drinks. She wants Stephanie to have a great time, and kind of hints the best way to get over a man is to get underneath another.

So i set it up, 4 day cruise. And there’s an incident each day, so i’ll split the stories up.

To catch our cruise, Steph and I drive all night to board our ship bright and early. We get in our cabin and first things first we open some bubbly and have mimosa’s. Cheers. Read more »

Wondering around the city to [M]y surprise [F] – Risky outdoor fun Part 2

Part 1: [https://www.reddit.com/r/gonewildstories/comments/f558ed/wondering_around_the_city_to_my_surprise_f_risky/](https://www.reddit.com/r/gonewildstories/comments/f558ed/wondering_around_the_city_to_my_surprise_f_risky/)

Thanks to those who were interested in part 1! Thought while I had time I would share part 2

So since this time I had her number we had been texting back and forth quite a number of times for a bit of fun and we weren’t dating but more like FWB. She was really into sexting which always made it interesting so one day, while I was at work, she decided to see how far we could take things. We did love to tease each other and it was always about how horny we could get the other person without sending pictures. Chat started pretty standard with how much we wanted each other and talking about all the things we wanted to do to each other, then we decided to step it up a notch and started saying things like I really want to fuck right now, and I just want to suck your dick so much right now. Now for some context I was at work when this was all going down so I was horny AF at work and this was definitely not helping me at all and she was also at work at the time. This is when it popped into my head that we should just meet somewhere and have a bit of fun! Read more »