Category: gonewildstories

My First Time: Anal [MF]

*Context: Based on the the DMs and questions I’ve been getting – which I fucking love by the way – I started thinking about writing a series of posts about my first times. E.g. my first blowjob, first time having sex, first threesome, etc. I can’t post things here that happened when I was under 18, so I’ll probably write those up and post them elsewhere, maybe on my Patreon.*

*(I’ve previously written about my first time with a girl, which was in college, and my first time touching a boy, which was in high school so I posted to Patreon.)*

*You know me… my name is Riley. I’m 26 years old, and a bit of a girl-next-door type. Specifically, I’m a 5’4” brunette with brown eyes, I wear my hair long, a bit past shoulder length, and I stay pretty toned with cycling classes. I’m no supermodel, but I’ve never had trouble attracting a guy (or even a girl).*

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In between my senior year of high school and college, I was dating a guy named Taran. He was tall, like 6’4”, lean, and played on the basketball team. White guy, smarter than your typical athlete, but just into having a good time. Read more »

Success — My first squirt [FM]

I cannot remember if I posted and he responded, or if it was the way around. What matters is that this was my first time meeting someone from here, but we were practically neighbors. Meeting up took no effort. We met up on the street near where we lived: we promised this was just a date in public to see if we felt anything, to appease our nervousness.

As soon as we gave each other a greeting hug, I knew I wanted to feel our naked bodies press together. I was proud of myself that night, however: I was conversational, trying to understand why we were both entertaining the idea of fucking a stranger from the internet, when all I wanted was to hunt him and taste all of his flesh.

We waved goodnight, but not for long.

With a simple email, he came over to my place, where he promised he would follow my lead and only go as far as I wanted. I thought we might make out, get handsy, nothing too innocent but not too kinky either. Naturally, I was wrong. One kiss led to the shivers from his hand running down my back, our mouths opening with wet curiosity, the pressing of my hipbone up against his. Before I knew it, I had taken off his shirt and was rubbing his hands all over his soft torso. He did not even try to conceal his bulge. Read more »

Married couple becoming Try-Sexuals [MF]

Just a little backstory.. wife and I have been married for 11 years now, things in the bedroom were never all that “wow” but they were decent. We went through a few dry spells here and there, as I imagine most married couples with kids do, but about 6 months we went through a huge dry spell and this instance brought on legitimate arguing and fighting and not talking for a few days. It finally came out that both of us were very sexually frustrated and needed things to change.

So we made an honest attempt to put together a list, individually, of things we want/need/want to try etc So if we both had the same or similar things on the list, they were put on our “Try List”. And then we each added a couple of selfish things that we really wanted to try regardless if the other person wanted to or not. We agreed to try everything at least once and if we liked it we would make an effort to keep those things going in the bedroom. If neither of us liked it, well at least we tried. If we sort of liked it or one did and one didn’t, we would give it another go. Some things on the list have been rougher play, extended teasing, degrading dirty talk, public endeavours, threesomes, swinging, meeting up with a random guy from raobj here on Reddit, etc there’s a lot more but just to give an idea. Read more »

19 [F] college student taught a highs school lesson

*Little description details, Cooper is a 27 yo high school teach that I found on tinder. About 5’10 black hair, muscular, overall sexy as fuck.*

Cooper and I exchanged numbers and within a week are planning to meet up at his house after I finish my evening class. We had been texting every day, with each text seeming to get dirtier and dirtier. We shared with each other what we were in to and that I enjoyed being a bit submissive while he was more into dominating, so our tastes worked out perfectly.

The day finally came that we were planning to meet for the first time in person, and let me say I have never felt more excited for something in a long time. The whole way over to his house I could feel myself getting wetter and wetter thinking about finally getting fucked by Cooper. I decided to surprise him by wearing my hair in pigtails while wearing a short t-shirt dress with no bra and thigh high socks, which I knew he loved from previous pictures I had sent him. Read more »

Lana, the cougar from the office [MF]

I used to work in an office in a pretty big building. It was pretty casual there, and most folks got along with each other. One woman who worked there, however, immediately stood out to me. Her name was Lana. She was about 5’8”, light skinned, makeup and hair always done well, and her clothes couldn’t hide her curves if they tried. She had small tits, but the kind of ass you’d expect to see on a stripper, or a porn star. She’d never tell her age, but I did some digging and figured out she was in her late 40s, but with her youthful and often quiet demeanor, she could easily pass for a decade younger.

Lana and I never worked together much, but we did notice each other. I started to suspect she had a thing for me, too — she way she laughed at my jokes, the occasional hand on my arm, the way her eyes darted around the room whenever I dropped some risqué comment or double entendre. Read more »

Starbucks Blow Job [MF]

This was last month.

Law School was starting to kill me so I fired up tinder to see what trouble I could get into. Nothing I was looking for, just pretty girls looking for boyfriends. Until I came to Alexandra. She had three pictures one with her friends, one holding a beer, and one at the beach. She had long blonde hair, blue eyes with melted greens and yellows, her boobs were perfectly rotund, her ass was big enough to carry a coffee cup. Her bio had one sentence: “Not looking for a boyfriend”

I shamelessly super like her and wait.

A little about me: I’m 5’10” with black hair and brown eyes, im a regular at the gym with abs and a really nice ass. I’m Bisexual and im pretty open about that fact.

Anyway, we match maybe a day later. I waste no time and launch into my best flirting.

“I’m glad we’re both not looking for boyfriends.”

“Yeah.”

“Makes it easy to sleep around.”

“Right?”

She wasn’t into it yet, but at least she was responding.

“I bet I’m better at sucking dick than you are” Read more »

My ex and I used to do some hardcore consensual non-consent ageplay [M]31, [F]29

This story is about the sex I used to have with an ex. We both liked incredibly unbalanced power dynamics, and to enable these we would frequently role-play her as a very young girl being raped by her father. If you might find content like that disturbing, I would suggest this story is not for you. We were both consenting adults, we had a safe-word, and we had discussed the scenario in detail beforehand. Neither of us had ever suffered abuse, nor naturally would ever dream of abusing anyone. We were just kinky as fuck.

My ex was five nine, blonde hair down to her shoulders, blue eyes. Full breasts with large nipples on an ex-professional-cheerleader’s body. I’m six foot, slim/toned, short brown hair and a five inch long, five inch wide cut dick.

Again, if you have a history of abuse and feel this content might upset you, please take this warning and do not read on. This is a story for people who enjoy severe disparity in power dynamics. I’m posting it here in case anyone else on the big wide internet enjoys the same sort of stuff, and gains pleasure from our experience.

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That time I banged my Ex and GF in a threesome[MFF][Group](Long)

[M27]This is by far my greatest/ favorite sex memory. I relive it a lot to cope with my current DB situation. I’m gonna give a little bit of a backdrop/history before going into my story if you’d like to just skip to the good stuff go down to the ~>.

I’m male, 19 at the time, about 6,2 and weighted around 240Lbs. I wasn’t the most attractive person at the time. I was your typical teenage boy. Lots of time spent watching porn and day dreaming about sex and my wildest fantasies. I came from a broken home and I hung out with a bad crowd. We weren’t ideal citizens. I had fooled around with tons of women before I actually had sex. Late bloomer. I lost my virginity to one of the the females in this memory. We will call her Arya. We both had birthdays in August so we were 18. Nice tight ass and solid D cups. We had dated our senior year of high school. Every day after school she would suck my cock while I fingered her pussy. It was hard for us to have sex, we both had younger siblings so we were never truly alone. We actually had to schedule the day I lost my virginity around our parents work schedule(Funny story for another time). We ended badly as I found out she was entertaining other men. Read more »

[F]I slept with my manager—and she came hard twice

Alright so this story comes from over the weekend. For context, I used to have a huge crush on this manager, but I thought she would never be interested in me so I moved onto a male coworker. I excitedly told this manager I had asked him out on a date TO WHICH SHE FUCKING REPLIES THAT SHE WANTED TO BE THE ONE TO MAKE A MOVE ON ME FIRST. The guy randomly kissed my cheek before my shift Sunday, and I realized I didn’t get the butterfly tingles. I felt literally nothing from it. When I walked into work, I dramatically announced to my manager: “I’m gay.” And we were laughing about the whole thing at first. BUT WHEN I SAY THE TENSION WAS HIGH THAT NIGHT ooooh best believe it! I couldn’t take it anymore and flat out asked her when we were alone, “So after our shift wanna hook up?” And seeing her giggle and get flustered made me feel so much more than with the guy. After work we went to hers—after getting pizza—and just chilled for a while watching funny videos and sharing work gossip. Read more »