Category: gonewildstories

Cougar from my gym follow up story with role play fantasy [MF]

Hi, all. This story is a follow up from a post I made a couple days ago. See my post history to find it. For those who didn’t, or don’t want to read it, I met a cougar over a couple weeks ago in my gym in SoCal and eventually summoned the balls to talk to her and asked her out. She invited me around for a drink rather than go out for one. I had the best night of sex with her but if you want to know more, check the post.

I had no idea that people would enjoy the story as much as they did as I had a lot of people message me directly about it. We had met a week after our first encounter and this one is possibly even better than the first one, though our first night will always be my favourite personally. Read more »

[FM] A walk in the park…

After meeting for a drink on a hot and humid evening with a redditor, (who very classily slid into my dm’s like no one ever has) and getting thoroughly over heated by his kisses, as well as grinding against his leg in what I now realise was probably pretty obvious to the packed bar around us, we decided to take a walk.

After finding a fairly secluded bench in a nearby park, he fairly quickly grabbed me and lifted me onto his lap, straddling him. I should say at this point that I’m 5’2” on a good day, he must have been a foot taller than me, this was pretty easy. He pulled my dress up over my ass, and with the fairly skimpy panties I was wearing it left me feeling deliciously exposed. He slid one hand between my legs and started rubbing my clit, finding my spot in seconds, while we kissed and dry humped like teenagers. I was getting wetter and wetter, as he squeezed my tits, rolling my nipples through my dress, as he whispered all the things he knew turned me on, slapped my ass, then told that I was his slut, which I happily confirmed. I broke into a sweat, and started to grind harder against him, edging closer and closer to cumming. Read more »

How I lost my [f] virginity [fm]

I [25F] have been lurking here for awhile, getting myself off to all your stories, I’ve decided its time to reciprocate and share one of mine.

My second year of college, the night before Christmas break, this guy and I were the only ones in our friend group who hadn’t gone home for break yet. We decided the only proper way to celebrate was to watch Christmas movies and drink in his dorm room. Drinking always makes me cuddly, so by the third drink and second movie I had started to curl up with my head in his lap. It wasn’t long before I could feel him getting hard under my head. I picked my head up and looked at his pants then up at him in “really?” sort of way.

“Sorry, I can’t help it, you are super cute right now” he said.

“That’s ok, I don’t mind” I said as I put my head back down.

But even as I said that, I couldn’t stop thinking about it. I had never felt a penis before and if I’m being honest it was kinda turning my on. I was so distracted thinking about his penis right next to my head I couldn’t even pay attention to the movie. It wasn’t long before curiosity got the best of me. Read more »

[FF] My First Time with a Woman (my roommate) – Part 3

This is a continuation of my first time experimenting with a woman. You may want to check out [part 1](https://www.reddit.com/r/gonewildstories/comments/ei4665/ff_my_first_time_with_a_woman_my_roommate/) and [part 2](https://www.reddit.com/r/gonewildstories/comments/eiccu8/ff_my_first_time_with_a_woman_my_roommate_part_2/) first.

After Mary fucked me with a strap on and had a very strong orgasm from the vibrator within the strap we took a nap together in her bed. I woke up and saw Mary looking at me. I asked how long she had been looking at me and she said only a few minutes but she liked watching me sleep that I looked so peaceful. We were laying in bed facing each other naked and we started just talking. I asked her when the last time she fucked a guy. She said it had been years but confessed to fantasizing about fucking my boyfriend Tim.

She started asking me what it was like to be fucked by Tim and how he compared to other guys I had been with. I told her that he was the only guy I’d actually ever been with and I loved having sex with him, but I didn’t have any experience with other men other than being being fingered and gone down on a few times by a guy in 11th grade. And right before I met Tim I hooked up with a different guy from school and he went down on me twice. Other than that all of my other sexual experiences were either with Tim or Mary. She was a bit shocked by that I think considering how sexual I am. Read more »

Classroom Threesome [MMF]

At the time, I was recently hired as a teacher in a local high school. I was without a doubt younger than the majority of teachers in the building, but still had around a 7 year age gap between myself and the oldest senior in any of my classes. I thought the age difference would prevent students from flirting with me, but little did I know that the student/teacher fantasy was one desired by both students and teachers.

Walking into a classroom with little experience is a difficult task. Any teacher will tell you that classroom management is the key to prevent you from losing your sanity. Most of my students at the time were wild and showed little respect towards me. Maybe it was my age, but it was probably the fact that I had no idea how to control a large group of teenagers. My skills improved over time as I learned each of their personality types and how to deal with them accordingly. Read more »

New Years- My whiskey dick date gets sloppy seconds [FM] [FM]

As soon as I got invited to a party for New Years I had to figure out who I was going to bring as my plus one. I had two guys I had been dating on and off but neither were serious at that point. I decided to take nick as my date only because out of the two, we had already had sex and I knew it was going to be a fun night.

Nick got back to me right away and asked if he could bring his roommate Brandon. He could be my roommate Jamie’s plus one so I said yes . Jamie is tall with blonde hair. Nick is tall and slender with black hair and blue eyes (and has a nice 8 inch cock ;)). Brandon is about 5’9 wild brown hair… the kind you want to run your hands in and green eyes. As for me, I’m about 5’5 curvy with DDs. Read more »

[MFF] My night with a Tinder date and the girl I picked up at a party beforehand

This is about 2-3 years ago. I was at a conference and, as you do, I got on tinder hoping I would find someone who wanted to spend a fruitful naked hour or two. I lined up a date (Mo) for after a party and went and got sociable… and picked someone up at the party (Emily).

First, to describe us: I am tall, burly and brown haired, with a scruff of beard that I maintain at a nice trim, and blue eyes. I’m average in the equipment department — a bit under 6″ — and I’m told I have a nice ass. Mo is medium height with wavy blonde hair, smoky bedroom eyes, and an absolutely killer ass. Emily is a skinny punk girl well under 5′ tall with no curves to speak of, but she’s got an intense sexy energy and a gorgeous, if rare, smile. Read more »

[MF] NYE quickie in a Hong Kong office

Long time lurker, thought it’s nice to share now.

True story: It was almost 10 years ago when I worked for a very small logistic firm. I had to work New Year Eve but the office let everyone go at 3pm (pretty standard practice in Hong Kong). It was 4pm and I was trying to wrap up my reports, my boss was hurrying me so she could leave, but without a client’s reply, I can’t finish my work. My boss finally said ‘fuck it, I have to leave, sorry for leaving u here on NYE…’ (that bitch…)

I had a 3rd date with this girl I was seeing and was eager to leave, she was waiting for me at a nearby coffee shop. Since I didn’t want her to wait by herself, I told her to come up and wait up here instead. My office overlooks the Victoria harbor, so the view was quite nice. You can imagine.

It was a cold NYE, but she (then 22) came up wearing a low cut shirt with a puffy jacket over it, a leather short skirt with almost knee-high boots. I never saw her dressed like this before in my previous dates, and needless to say, my jaw dropped…. Read more »

I blew my boyfriend for more than 2 hours straight [MF]

I posted this a while ago on a different sub using a throwaway account, but decided to edit it a little and post it here with my real account because it was hot as FUCK. Enjoy ;)

The following is a detailed account of what my boyfriend later described as a “life changing” blowjob. 

I [25f] was getting ready to drive over to the city where my family lives to celebrate thanksgiving, but I really wanted to give my boyfriend [30m] a blowjob before I left town because it’s my absolute favorite thing to do. I went over there and pretty much immediately dropped to my knees and pulled his cock out of his pants and into my mouth. I love to tease him at first by slowly licking his dick everywhere except for the most sensitive spot on the frenulum. Then I moved to his balls, taking one of them into my mouth at a time and slowly pulling it out so that it makes a smacking sound, “pop!” Finally, I wrapped my lips around his head and slowly took him into my mouth, head, shaft, all the way to the base, making sure to keep eye contact as long as i could. I fucking love how vocal he is during sex, little gasps and moans. I love the way his eyes widen and then roll back and his soft lips part slightly to reveal his teeth.  Read more »

[MF] Invited to sorority formal as a friend, turned into nice FWB fling

This is my first time writing anything like this. I’m not a regular follower and I realize this may not be so “gone wild” compared to some of what I see here. But it is a 100% real sex story that I remember fondly. Maybe some of you will enjoy it relate. Most of it I remember like it was yesterday. It’s quite long sorry.

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OK straight up, always a loser with girls/women. Total pussy, zero game, not a player/stud/alpha male/stallion, shy with girls, self-conscious, you get the picture. Average looking at best. 6 ft tall decent at sports growing up but got chubby (about 215lbs) by HS – not muscle. Sci-Fi nerd/Metalhead. No prize looks wise but I have other good qualities, very intelligent, good sense of humor, and a strong moral compass. Always try to treat everyone with respect including women. Never a problem making friends and overall was respected/liked by most people in various social circles. As horny and as big a perv as the next teenage male (maybe more) but only hooked up with a few girls in high school and no sex. My core group of friends and I didn’t socialize with many girls during HS (shocker). On a side note I met a nice and very attractive woman in my late 20’s and am happily married with children now. Read more »