gonewildstories Archives — Page 3841 of 5640 — NSFW story

How she turned from platonic coworker to an amazing fuck [MF]

This all happened at the beginning of July. It’s a big of a long read, but I’d like to set the foundation for the story. Maybe it’s too verbose, but ehh.

I had worked with Anna for about two and a half years. Not on the same team, but on the same floor of the same office. She’s 28, standing around 5’8″, packing a great ass, and 36D (according to her) tits. A brunette with great curves, a pretty face, and an attitude to match. While I had always thought she was physically attractive, Anna was definitely not my typical ‘type’. I had always dated women who were a little on the prim and proper side. We all know the type; Tight skirts, sly smirks. Anna however, was a jeans and cowboy boots kind of gal. She likes country music, rodeos, shower beers and iced capps (Yes, this is a Canadian story, and she is aware I’m writing this. And goddammit that sentence sounds like a country lyric). I’m 33, 5’11”, 185lbs, a half-decent build from weightlifting, and I’ve been growing my hair out; it’s thick, and peripherally relevant to our story. I’d like to think I’m a decent looking guy, overall. Pretty good ass for an Asian, anyway. Read more »

The day I [F]ound out I could squirt – [Long] [Photo]

This is the story of how I found out I could squirt. I’ve also included some photos showing me using the exact device that caused said squirt, and many more since ?

For about as long as I can remember, I’ve been playing with myself.

I don’t remember the exact age, but I know by the time I started puberty around age 11, I had already known how to orgasm for many years.

It was something I did atleast daily.

I remember on my 19th birthday, being recently single, treating myself to 19 orgasms by my own hands.

I never had anything to use except my fingers until my boyfriend at the time and I went to a sex shop around ten years ago, and we bought a back massager. Yes, the one I mentioned in my window washer story ?

This hand held ‘back massager’ changed my life. An orgasm from my hands was never anything like one from the vibrations of this machine.

It also lead me to trying other things like a shower head (also highly recommended to the ladies out there) Read more »

Afterclass ass [MF]

Another story from my time being the assistant for a self defense class, this story involves a wonderful girl name Emma. This is probably gonna run a little long so I’ll mark where the fun stuff begins. For kind of the whole explanation about me and the whole self defense thing here’s [the previous story and info](https://www.reddit.com/r/gonewildstories/comments/br3pdt/perks_of_being_the_assistant_in_college_mf/?utm_source=share&utm_medium=web2x) but other than that let’s get started!

Emma was this extremely charming girl from one of night classes, she had shoulder length brunette hair that was always either straight and pinned up or braided kind of like how Emilia Clarke’s hair is in Game of Thrones. Emma has a tattoo of a dream catcher on the back of her shoulder and a small sparrow just above her right hip. She had a fairly thin frame she was very much a tiny but fit girl. Emma stood around 5’3 with nice perky petite boobs and a small perky/tight ass despite Emma’s slender legs and body she was a tough girl and you wouldn’t realized it but was on her way in to the Police Academy. She was a bit of a tomboy but always energetic even on days she was tired. Honestly by this point I wasn’t surprised there is always that one girl in class who was pretty much into pain or was of the mindset of “I can handle just as much pain as I can dish out”. Don’t get me wrong it was nice because they were always the ones more willing to either volunteer for demonstrations or actually take a hit but at the same time, they were also the ones who dished out the hardest which is fine for me but not so fine for other students lol. Read more »

My Landlord’s daughter Part 4 [FF]

This one is about the first time I fucked my little slut in the ass.

We had often talked about me fucking her anally. She was a bit hesitant at first as she thought it would be really painful. One evening, after I had fucked her pussy and she was busy licking my strap on clean, I asked again if she wanted to try it. She said yes.

I had her get on her knees and elbows. I lubed up my fingers and began to finger her tight, virgin asshole. I was gentle, at first. She moaned softly and seemed to be enjoying it. I added another finger and kept fucking her. She groaned and whimpered but begged me to keep going. So I did.

After after adding a third finger and stretching her hole for a few more minutes, I decided she was ready to get my strap on in there.

Teasing my boyfriend with my favourite outfit [MF]

(Sorry if the formatting is off, using mobile!)
So I had been posting on reddit for a little while at this point, and my boyfriend had seen one of my outfits in pictures but not in person. I decided I would pack it and take it to his house with me, and if I felt like putting it on for him I could. Come Monday night and he’s just about to start playing DnD with some friends over voice chat. I decide this is the perfect time to put the outfit on, so I pull it out of my bag, show him the skirt and then wander off to get changed.

By the time I get back into the room he’s in his voice chat with his friends. He looks up at me approvingly but doesn’t say anything as his friends would hear him. I sit down next to him and go through my reddit feed for pretty much the entire time that he plays DnD. I wanted to just lean over and pull his dick out of his trousers and start giving him a really sloppy blowjob, but I’m worried his friends would hear so I just sit quietly and notice that he’s looking over at me a lot, running his hand over my thighs every now and then. Read more »

My best friends mom. Part 2: She wants to watch. [MFF] kind of.

A new week, a new chapter in the Best Friends Mom arc. In the last story I mentioned how my best friend Airin, hooked me up with her mom Lisa, because we both just went through bad break ups/divorce. So we went out to a bar where we danced, another where we kissed, then back to her apartment where we had the best sex I had ever had at that point in my life.

So what happened the next morning? We woke up together. We both agreed we’d have to do it again some day. She gave me a kiss and sent me away. The unfortunate part was having to do the walk of shame back home and see Airin.

As expected Airin was there with her girlfriend TJ. They’d been together for a while so we were close. That’s why I had no problem with her when she said, “Ah yes the walk of shame.” Airin and TJ sat on the couch when I came home and began the 100 questions. Going from “How was your date?” to “Where did you go?” And TJ with the question of the hour, “Did you fuck her?” But I simply said we had fun that’s all that they needed to know. Airin hugged me and said “Thanks for taking her out. She really needed it.” And with that my first encounter with Lisa was over. Read more »

[MFM] Once Upon a Time in…. [SUCCESS]

In the valley

Narrator: When two guys who have been friends for so long, someone who is more than a brother but less than a wife, there is only one way to bid farewell. A good old fashion tag teaming.
[Enters car]

Buchanan Brothers – “Son of a Lovin’ Man” ? I’m the son of a loving man My daddy told me Get you all the loving you can And I can cause I, I’m the son I’m the son, son, I’m the son, son I’m the son, son, son of a loving me?

Arriving at hotel. 20mins later

[front desk supervisor] Am so sorry but our system is down, (looks at Gloria) Gloria please give him a room and finish the check in later.

Narrator: Our first character finally checks in and sets up for the first woman who is on her way for a night of double pleasure. As the first woman arrives five minutes later and texts to find out what room to go to. Read more »

She put on fuck shows for me across the alley [MF]

I lived in an apartment in the attic of an old house. Across the alley was a three floor walkup. My kitchen window was the only one that could see into the top corner apartment.

A young couple moved in. I piled books up against my window. If they checked who could watch them, they would see one window and nothing but a stack of books piled up behind it. I removed, one book, leaving me a slot to look through.

They didn’t have furniture. They didn’t have curtains. One evening, when they got home — and they always got home really late and together, as though they worked at a bar together — they dragged the mattress from the bedroom out to the living room so they could watch TV on it. Their lights were out, but in the occasional flicker of TV light, I could see they weren’t watching the show. Her feet dangled in the air and I could see his blue-lit ass between them. Later I could see her swaying back and her shoulders pushed up riding him hard. Read more »

She fucked him in the tent so hard she pushed right against me [MFM]

Keith suggested camping. There was one big tent. He seemed keen to make sure Joanne was going, and Joanne seemed to be making sure I was going. It looked like all four of us guys and her were in, but by the time Saturday came, it was down to just Keith, Joanne and myself. I tried to back out but Joanne wouldn’t let me. I was curious about why. I was trying to gauge Keith on this, but I couldn’t read anything.

I was staying in a cabin outside a small town with four student friends. We were looking for summer work. Joanne, the one girl, was from Quebec. The way she talked so openly about private things made the rest of us embarrassed and she would laugh at us for it. She was so free, and years ahead of us in ways.

She wore long brown hair that hung around her shoulders like a shining curtain or a cape. She couldn’t talk without it sounding like breathy porn and she couldn’t smile without it looking like everything had a hidden sexual meaning. Read more »