A [F]reshly-packed bong and just about anything I can find sliding in and out of my asshole

I’m out in the middle of nowhere (well, maybe not the middle, more like the edge of nowhere), so what else am I supposed to do but get high and experiment with anal? Well, experiment I did; now I’m basically the Marie Curie of anal masturbation.

To confess: I used to not understand the very idea of anal. It seemed gross and unneeded. Until one night, stoned and alone in my bedroom, big headphones on, watching porn, I fell down an anal porn rabbit hole. I was convinced it was all for show, some weird thing only porn star did to excite confused teen boys.

But as I lazily played with my puffy pink pussy, I thought “why not?” and slide one finger a little lower than normal. I had worked myself up to the point where my pussy was quite creamy, so my wet fingertip against my asshole felt strangely good. It was sensitive and it made me shiver a bit, but I felt a white-hot desire to explore farther. While the woman on my computer screen took a massive cock inside her puckered ass, I pushed lightly against my whole hole. My little asshole seemed greedy for my finger, slowly enveloping it as I pushed further. By this point, I knew I had found something fun ?

Chloe: or Getting Over My Daughter’s Friend Jenna [MF]

I drove Jenna home after we cleaned ourselves up. She reached across my SUV and stroked my cock through my pants on the way there. I was so ready for round two. Just looking at her made me hard. Her skin had started to tan as the summer drew nearer giving her an olive complexion that complemented her freckles. She seemed so feisty and full of charisma that night. 

“That was fun.” I said as we pulled to her drive way where the party was still going. It wasn’t until I saw all of the girls’ and their parents’ cars that I remembered we might have to explain this absence. I felt a lurch in my stomach.

“No.” She replied with a teasing tone in her voice. “That was dirty. That was wrong.” She winked.

“What are you going to say if someone asks where you went?”

“I’ll just tell them I had a date.” she offered smugly. 

“Jenna, what are we doing?” I blurted out, unable to keep my thoughts and my words separate any longer.

“We’re just fooling around. No strings, No feelings remember?”

Theatre wank [M][mast][exh]

For such a big city it was odd that there were no adult bookstores or arcades. Shitty internet in the Air BnB, nothing would stream. I needed to blow a load and my repeated solo wanks in the bathroom had grown boring.

One theatre showing porn, that was it, in the whole city. It was written up as a bit of a cruising spot, but only late night once the parade of tourists had quietened down out the front and some anonymity could be maintained. Not that I was looking for company.

Waited until at least close to dusk. Odd setup. Old style movie theatre foyer, ticket booth, like they were trying to legitimise the venue. The large “XXXX” signs out the front kind of gave it away, not to mention the sounds of on screen fucking coming from behind the curtains to the stalls. Bought my ticket from the disinterested staff member watching football on his phone and went in.

Stuck to the back rows as advised by the blogs that had reviewed the place. Plenty of space between the rows so no need to bother anyone as I shuffle past. More to the point, those that had their cocks out were happy to display their hardons to all who would take a look.

Repressed Catholic girls are the best! Story of [M]y wi[F]e and our first weekend alone together.

[Reposted because it was removed]

Chelsea is the living embodiment of the Catholic School girl stereotype. I’ve wrote about our encounters on several occasions in the past but I’ll quickly recap. I want to be clear, ***she was over 18*** when she started to experiment, have a boyfriend, act out on all her years of repression. But like the stereotype suggests, she snuck around, lied to her parents, smoked behind the bleachers. She even had a second pair of clothes in her bag so that she could change after school. After she graduated, she remained a “*virgin*” by giving regular blowjobs and having anal sex with her b/f because it was a religious loophole. You name the repressed fetish, she pretty much had it. Because of her ultra-religious family and strict adherence to proper etiquette in society, Chelsea wore a “good girl” mask nearly 24/7 all throughout college and continued it when dating me.

A Series of Exploration Part 1: The Ex and her friend. [mff]

I intend on writing different parts to this story, each describing an encounter that changed my life.
I’m at a point in my life where I’m more confused than ever. This last year has left me wishing I had a clear answer for what I wanted, what my morals and values are, and what I deserve for my actions. Maybe recounting these critical moments in my life will help, maybe your comments will guide my emotions.

I’m a slow burn kind of guy. Just a warning that these will be long, with more build up than most stories I’ve read on here.

This is the story of my Ex, her friend, and a college dorm.

But first, some backstory

_________________________
Jess and I had met while volunteering at an afterschool day care. I was the excited 8th grader, and she was the innocent 6th grader. We became fast friends and the kids would tease that we’d be together forever and ever.

We took turns admitting to each other our feelings, and subsequently took turns denying the feelings and using the age difference to justify avoiding each other. I was heading to high school, much to old to be dating someone in middle school, right?

The Camgirl Part VI: A Private Showing [f] [solo] [ff-ish] [exh] [voy] [mast] [anal]

VI: Blake

Blake chewed on her lip as she inspected her reflection. Her makeup was perfect—black, wing-tipped eyeliner with a hint of blue eyeshadow brought out her eyes, her lips were a deep red, and a light dusting of blush would make her look more aroused than she was. She doubted anyone watching her show noticed the subtlety of her techniques, but she knew from off-screen tests that they worked very well. Her hair was as radiant as ever, as she had re-dyed it a few days ago, and the deep blue of her thong—in an older fashion where the sides rose to hang high above her hips, almost at the cleft of her waist—matched. The stockings she had chosen for this show went higher up than most she owned, just short of where her thighs met her hips, and for a top she wore a thin, white shirt with long sleeves that she had cut off just below her breasts. As usual, she wore no bra, since she had no need.

Another story from my clinic [MF]

I’ve posted a few stories here before, here are links.

[https://www.reddit.com/r/gonewildstories/comments/aam4yk/what_an_amazing_day_at_the_office_mf/](https://www.reddit.com/r/gonewildstories/comments/aam4yk/what_an_amazing_day_at_the_office_mf/)

[https://www.reddit.com/r/gonewildstories/comments/bqk4y9/another_great_day_at_the_office_mf/](https://www.reddit.com/r/gonewildstories/comments/bqk4y9/another_great_day_at_the_office_mf/)

This one describes another encounter in my clinic.

My clinic is in a 3 story office building. I’ve described that I’m happily married but my wife has health issues that preclude a regular, vigorous sex life. But when we do have sex, it’s good. There’s something special about making love with someone you genuinely love. But, there’s also something special about fucking a dirty little slut who wants to be your fucktoy. Just different pleasures and I greatly enjoy both.

There is a hispanic woman who is on the janitorial service. I think her shift is something like noon to 8. Her name is Margarite. I’m guessing she’s late 30s, early 40s. I’ve spoken with her a few times, she’s a nice lady, never remotely had a sexual thought about her, though my sense is she’s interested. Could be reality, or just my delusional male ego talking. She’s reasonably attractive but could stand to lose about 10-20 pounds. Not particularly athletic looking, which is really my type. But medium breasts, reasonably firm, and a decent ass. Trust me, there’s a reason I’m sharing this. I’ll be circling back to her in this story.

After almost a year of experimenting with hotwife/sharing, the story of the first time my Japanese ex-wife and I had a full-on threesome [MF][MFM]

So, I previously shared the story of the first time my ex-wife and I experimented with sharing:
https://old.reddit.com/r/gonewildstories/comments/badf0f/the_first_time_my_japanese_exwife_and_i_branched/

As you can gather from how much we enjoyed it, we did not stop there. Still, for almost a year, it was always her having sex with another man privately, and me just hearing about it and seeing pics afterward. Finally, on a trip back to the US, I ended up sharing her with another old friend of mine who was completely up for doing stuff with all of us there in the room together.

For me, it was brain-meltingly hot, and like the last story, it was another major line crossed in exploring that side of sex.

Obviously it wasn’t a spontaneous thing. He had heard the stories from my other friend, and we’d talked about the idea of passing her around the group in the leadup to that visit home.

By that point we’d been there for probably a little over a week, and she’d already been with with my other friend (the one who had visited Japan and fucked her) and two other friends of mine who’d been asking for a turn with her for months, continually checking when we were going to visit.

Be[F]ore I [M]arried my Catholic School girl, we had an epic First time Overnight weekend.

Last night’s hot experience with my wife inspired me to write about another gonewild moment between us. I’ve wrote about our encounters on several occasions but I’ll quickly recap. Chelsea is the living embodiment of the Catholic School girl stereotype. Grew up in a repressed home, spanked constantly as a child all the way to HS (and grew to love it as a fetish). Remained a “virgin” all through her teenage years by giving regular blowjobs and having anal sex with her b/f. You name the repressed fetish, she pretty much had it. Because of her ultra-religious family and strict adherence to proper etiquette in society, Chelsea wore a “good girl” mask nearly 24/7. It was when she was alone and with me, did she finally get to show her true self.

Sex with my boss’s wife – last one removed, had to resubmit as one post, sorry it’s so long [MF][MFF][FF] [Long]

Broke this up in parts to make it easier to read
Part 1

Some background that I think is pertinent. I have worked for the same guy for 12 years now. During that time he and I, along with our wives, have become very good, close friends. Also my wife would identify as bisexual if she wasn’t concerned about how other Mom’s, PTA parents, etc would perceive this and by extension us. Last two things this is a throwaway account. I have been going back and forth on whether to share this experience for a number of reasons but finally decided to jump in with both feet.