My best friends boyfriend took my anal virgintity [FM] (BDSMish)

This is my first time writing something like this, so go easy on me!!My best friend, (we’ll call Catie) and her boyfriend (John) go to school in a different state. I miss them, and they flew up and visited me for my birthday.

Fast forward to my birthday party, and we’re all super drunk and playing Never Have I Ever. When it gets to me I start with “Never Have I Ever been fucked in the ass”. Catie mumbles something about me missing out and takes a shot. She comes up to me after and starts telling me I should try it, going on about how great John is in bed, etc. I had just gotten through a nasty breakup and was getting jealous and upset. She saw it on my face and whispered: ” John thinks you’re cute, it’s your birthday, go have fun”.I asked her if she was sure. She nodded and waved him over to us. After all three of us talked for a bit, she asked to go to sleep in my spare room. Read more »

[M]y Cock Slicing Into The Perfectly Round, Smooth Ass of This Delectable 21 Year Old Blond [F]

I posted this story awhile back but didn’t know how to paste it and keep the paragraphs. Figured that out, it’s much more readable. Hope you enjoy. It’s factual.

So here I am, looking up for a second at my reflection in the mirror, contemplating how in the fuck I have arrived at this point after 53 years of life. Standing beside my bed, looking down at my cock slicing into the perfectly round, smooth ass of this delectable 21 year old blond, while she pulls mightily on my sheets clutched in her fists, groaning and squealing with each thrust. Amazing. My age and fucking this girl young enough to be my granddaughter. And she’s loving it. Read more »

While Hiking One Day

It’s one of those moments in life that you can’t plan, they just happen.

After some light hiking we are left standing on a small rise overlooking the sunbathed forest, enjoying the moment. Not touching, but close. We are both flushed and warm, our skin glowing from the combination of the sun and the effort of the climb.
I look around and see a large patch of grass a short way down the slope. I don’t say anything, I just go. I sit, remove my shoes and socks, and lay back, allowing my back and head to rest on the ground. The angle of the rise makes it feel like I’m relaxing in a lounge chair. I plant my feet on the ground so that I can feel the cooling effects of the grass between my toes.

After a few minutes I hear movement, and then a shadow falls across my face. I open my eyes to look up and there he is. With the sun coming from behind him, framing his head and entire body in golden light, he looks like a featureless Greek god. I’ve always found him beautiful, but in this moment he is irresistible. My breath catches unexpectedly and I feel a knowing tingle between my legs. Read more »

[MFM] That Time I Hooked Up with My Roommate’s Brother and His Friend (Part 1)

If you haven’t read the last two stories I wrote, about [how playing matchmaker](https://www.reddit.com/r/gonewildstories/comments/brqo2k/fm_playing_matchmaker_has_its_benefits/) for my college roommate and the guy she liked [got me some amazing sex](https://www.reddit.com/r/gonewildstories/comments/bws2nf/fm_playing_matchmaker_has_its_benefits_part_2/), I recommend checking them out. People seem to like them.

This is about something different though and it’ll hopefully be a bit shorter. (*Narrator voice*: It wasn’t)

That story happened about 10 years ago and a lot has happened to me since then. I’ve had a lot of great (and some not-so-great) relationships, met the man of my dreams and even gotten married.

But once I had my tryst with Chris, I came out of my shell. I realized that it wasn’t that I didn’t like sex, but rather that I just hadn’t experienced how amazing *good* sex is.

Throughout that whole time though, I’ve always had a pretty voracious sexual appetite. On top of that, I really like trying new things. Luckily, my husband does too. We’ve been together for almost 5 years so we’ve built up enough trust that we can both feel comfortable letting our freak flags fly in the bedroom. We’re both pretty willing to try whatever the other person suggests. Read more »

I [M] Ate Out a Black MILF’s [F] Sweaty Bush from Reddit (RAOMD) in Her Hotel’s Sauna

Because I got so much love on my last post, I thought I’d tell another one of my many sexual encounters. These are all 100% true!

So, after posting and replying for ages on RAOMD (random acts of muff dive), I found a post from an older woman (30s) who was travelling to my city and wanted to receive some NSA head ASAP. I responded quickly with my pics and kik as she requested and she added me and we started talking. She was 30, black, pretty thick but not out of shape and very professional looking. She was in my city for business and she had finished her meetings for the day and wanted someone to meet with. It was about 9pm when we started talking and she had a flight to catch the next morning so she wanted to meet ASAP as long as I proved to her I was real and clean which I did. Read more »

[MF] discovering my cute classmate’s wild side (cheating)

At the college that I went to, they had a program where freshmen could take classes in the common room of their dorms. This obviously made things incredibly convenient for students; we could simply roll out of bed, and stroll down to class in our PJ’s. Not only that, but it allowed us a great opportunity to meet people who lived in the same dorm. As a horny, young college student, that was the real draw.

In the very first day of my in-dorm Greek Mythology class, I found myself instantly attracted to one other student in particular, let’s call her Kristin for the the purposes of this story.

Kristin was tall and lean, with slightly curly red-brown hair. She had milky white skin, and a mischievous smile. The first day of class, she was wearing exercise shorts and a black tank top. I couldn’t stop tracing lines up her legs with my eyes, up to her flat stomach and perky breasts. A pink push up bra was just visible under her tank top. I’m sure I spent a little bit too much time staring, because at one point she caught my eye and smiled. Read more »

Orange you glad you fucked you [MF]

I’m not sure how she caught me

I was grocery shopping and she kinda came out of nowhere. I was putting some bananas in my cart and she was getting some apples.

Her ass was fantastic. She had on deep black yoga pants, and they did nothing to hide her own apples sticking out.

I looked away quickly because I was staring, I’m sure I didn’t give her a chance to notice but she came up to me and said “you should see it when there’s nothing to block your view”

I chuckled “sorry for looking, I couldn’t help myself”

She smiled and said “it’s appreciated”.

So I went about my shopping thinking about her ass the whole time. The ass was the least of my worries though, she had a rack that you could dive in.

I somehow made it through the checkout line lost in thought when she stopped me outside.

“Hey I’ve got some time to kill, why don’t you follow me home and help me with the grocery bags”.

“Lead the way I said” smiling as I got in my car and followed her home. Read more »

Groped, Betrayed, Blackmailed PART 2 [blackmail],[NC] [FF] [MF]

Earl watched as Lisa almost crumbled to the floor when he showed her the video. He had asked her to stop by his house after school one day and give him an opinion about some remodeling he was doing. His wife was out of town, and they would have a couple of hours to themselves. More than enough time.

With the video playing over and over in front of them, Lisa listened , dumbstruck, as Earl told her what she was expected to do. At first she tried to reason with him, telling him there was no way she could go through with it. He simply drew her attention to the TV screen, where she was in the throes of passion as the blonde buried her head between her legs, and then watched as Lisa returned the favor. How would her husband react if he saw it, How would her employer react, her friends ? Where would she go, what would she do ? Soon , Lisa was listening carefully, the two of them working together to figure how to lure Vicki into the trap. Read more »

[M]y [F]riend the Teacher (cheating) #2

As I posted previously, what started innocently and over many months soon turned torrid. In many ways I was wanting and hoping for this, what I didn’t know was how intense her desires were and how they would intensify over the coming weeks. Nor did I know that by doing what I love to do to a woman I would be unlocking something inside of her I am not even sure she knew was there to start.

After our first romp I thought maybe she’d slow down, pull back some, but I was mistaken. Later that night I got a text from Sandy. “My pussy is still throbbing from this afternoon,” she said. “Overtime I think about what happened I get wet and can almost feel your big cock back inside me. No man has ever made me feel like you did today. Thank you for making me feel like a bad ass woman and for sharing yourself with me. Here is a special treat for you and what I want to do to you next time!” Attached was a picture of her on naked, squatting down, pussy lips exposed and open as if she were riding me. Read more »

The Curling Iron (or: how my daughter’s friend and I seduced each other), Part 1. [MF] [First Person]

“*Really?*” I repeat to myself, pacing around obsessively enough to set the floor on fire. “*Are you really becoming that guy?*” It’s not long before all that mental energy is redirected to wiping this stupid—and increasingly perverted—grin off my face.

I’m failing. Hard.

She’s coming over. She’ll be bringing those strawberry blonde curls, those green eyes that I can already feel piercing my soul, that silky porcelain skin, and the leggings that cling to those curves practically engineered to make my heart burst out of my chest. Never mind what they do to everything *below* my chest.

“Repeat after me”, I whisper to myself, scoffing between every word at how corny I must sound. “She’s 18—that’s legal. You’re 42—that’s *creepy*.”

And, of course, what makes it so fun. The chase, with a whole lotta taboo on the side—neither of which I’m allowed to indulge. But it’s too late. I’m officially that guy. The guy attracted to his daughter’s friends.

And, of all times, during the summer before college. I’m praying that my self-awareness—of the laughable cliché that this situation is—can overpower the shakiness hitting my legs the minute I hear the doorbell ring. I take a deep breath. I turn to the kitchen table and start to fumble around, looking for the curling iron she left at last night’s sleepover. She’s here to pick it up. Read more »