I [M] finally built up the confidence to ask to be pegged by my girlfriend [F]

Sometimes I am a little shy about bringing it up, but my girlfriend knows that I enjoy assplay. Most times I use texting as a form of communication asking to play.

But today I walked out of the shower after cleaning myself up and straight up asked her to peg me. Her eyes widened and said “Of course!!”. I went to the bedroom while she was finishing up a show, so I had time to put my prostate massager in to get myself warmed up. After about 15 minutes putting together the strap on (we took it apart to throw it in the wash) I finally got it all assembled and ready then she put it on.

She asked me to sit on her with her legs hanging off the bed. It’s about 7.5 inches and thick so I wasn’t sure I’d be able to take it fully, but I mounted her and slowly squatted down until I was sitting on her lap. After a moment to adjust to the feeling I started to bounce up and down trying to find the best angle and thrusting movements. We move through multiple positions… me standing with her behind me, her standing with me on all fours on the bed, on my back with legs up, and then me riding her cowboy style.

[M]y [F]iance – The Gift

This happened a few weeks into January this year.

Grabbing the mail as usual, I was surprised to see a priority mail package. It was on the smaller side and had no return address. Interesting! Back at my desk, I tossed the pile of ads in the trash and opened the box. Within was a small, sealed package, instantly (in a way) identifiable: It was a dark blue/gray box with a picture of a prostate massager on it. In the top left corner, I read it was by a company called we-vibe. Eager to open it, I sliced at the wrapping. Soon, I had the USB charger, instructions, silky white carrying bag, and dark blue massager in my desk. Also in the box was a note that read: For our remote enjoyment: Read instructions! Your Lover.

Interesting, but who sent it? It could have been Ellie, Jim, or Lucy. Do I risk asking one and upsetting them or wait and pretend not to know? I looked up online to see what the toy was. It was a Bluetooth remote controlled vibrator called The Vector. Apparently, it could be controlled by anyone with the app and permission to connect. This could definitely mean remote fun!

New Army Boi [Part3] [Gay] [Kinks spoilered at top of post]

*This is part two of the* ***New Army Boi*** *series, Part 1 can be found* [*here*](https://www.reddit.com/r/gaystoriesgonewild/comments/lwlv0l/new_army_boi_part1/) *, Part 2* [Here](https://www.reddit.com/r/gaystoriesgonewild/comments/lx1v3h/new_army_boi_part2/)*. This entry features some more kinks, in order they are:* >!Chastity !<, >!Piss drinking/play!< , >!Gay-pegging!< *And some* >!rimming!< , *not really a warn-able kink but heyo thought I’d mention it ;)*

*If you have any kinks or ideas you’d like seeing put to word, just shoot me a message with details! I’m very open to requests and would love to help bring your fantasies to life on the page.*

*All characters are consenting, over the age of 18, and purely fictional.*

*Enjoy :)*

You wake up with the other recruits, most of them with tents pointing straight from their crotches, but none of you have time to deal with them. You turn onto your side, looking at your clothes. You rub the sleep from your eyes and as your vision focuses your stomach drops through you. On top of the pile is your key, snapped in half. Shit, you think. Taking a deep breath, you glanced around and surely enough every other recruit still had a copy around their necks, dangling, taunting you. You dress yourself quickly, being barked at by multiple officers at either ends of the room. You have no time to revel in the power, righteousness, and pure sense of being that comes from your uniform before you rush out with the rest of the recruits.

[MF] – Fucked by my wife

My wife and I have been together for over 20 years. Like any long-term couple, our sex life has been full of twists and turns, but now that we’re into our 40’s and have learned about each other’s (and our own!) bodies, the sex has been pretty damned good. For many years, sex was generally satisfying but also pretty “vanilla”. We’ve always enjoyed our lovemaking, but never felt ALL that comfortable discussing sex, each of us being just a little shy about expressing our desires. I’ve always had a bit of a stronger sex drive, but she also has her moments where she shows her inner minx and sometimes really takes control when the mood is right.

Over the past few years, I’ve gotten into prostate play during my private masturbation sessions. I started with an Aneros (a couple different ones), and while they were nice, I never hit “the big O” from anal stimulation alone. For a year or so, I tried to learn how to get that hands-free orgasm I’d read about, and while I’d had lots of good sensations, I was never able to get over the edge without jackin’ it. While my wife was aware of my toys, I kept them to myself, and she was content to let that be “my thing”.

I never felt more bisexual

A bit of background first.

So, I (M, 30) have been in a pretty deep self discovery journey over the past few years. It all began with me listening to my then girlfriend (soon to become wife) talk many times over about the fact that she would like to try sex with other girls. Over time, that made me feel safe enough to question my own sexuality, and ultimately sent me down a long path of asking myself if I felt the same way about other men.

In parallel to that, I began to feel more and more curious to truly know what women felt during sex. I asked myself: how must it feel to be penetrated, or to have a vaginal orgasm? I have never not loved being a man during sex with my girlfriend, but at the same time what she felt seemed so fucking great and so different from what I felt… It was alluring, and I began to really want to have a taste of that, in addition to what I already had.

I eventually figured out that the best way to pursue this would be to engage in anal play, and so about 18 months ago I bought my first buttplug/prostate massager.

A Blowjob for The Birthday Boy [MF] [Cons] [Oral] [Cumslut]

Jen finishes tidying up her apartment, sticks a bottle of prosecco in the fridge, and pulls out the little gift-wrapped package from her closet and puts it on Dane’s plate at the set dinner table. It’s Dane’s birthday. Jen wanted to plan an elaborate party, but he specifically requested a simple dinner for two, so it’ll be the best dinner for two she can make it.

Her career’s been going well and Jen recently upgraded to her own solo flat, no roommates. It’s been great for her work from home concentration, her independence, and her sex life. She’s in her own little slice of paradise. It’s a corner unit in an old building on a tree-lined street in a much nicer neighbourhood than she’s lived in before.

[MF] My boyfriend finally admitted his bi past

I’m a bi woman and still have the occasional bi partner which my boyfriend is aware of. He’s very submissive and based on his kinks I’ve always had my suspicions that he’s, at the very least, bi-curious. We’ve talked about it many times and he’s always said he’s never had any experiences with guys. Either way, I am completely fine with it. The reason I’ve asked so often in our relationship is because of his dirty talk and the things he’s interested in doing in the bedroom. Well…..I finally got him to admit that before we dated he blew a guy once and was a bottom one time as well!!

Here’s how it went down:

I was going down on him while toying his ass with a prostate massager. As we usually do, the dirty talk commenced. He was moaning a lot, but his words are what made me pause. Summarizing here, but, pretty much what he said:

[FM] My boyfriend Henry and I try some light femdom and edging on for size

As I mentioned previously, Henry and I had a fun, naked, [free use weekend](https://www.reddit.com/r/gonewildstories/comments/h8k42p/fm_my_boyfriend_henrys_30m_and_my_28f_quarantine/) as a way of spicing things up after a [friend](https://www.reddit.com/r/gonewildstories/comments/gvlx1f/fm_my_boyfriend_30m_and_i_28f_put_on_a_socially/) moved out of our apartment. At the end of the weekend, Henry confessed that he wanted me to try taking charge and incorporating possessiveness more in our sex life. We agreed to a new 24/7 free use rule for giving oral, and we started taking advantage of it immediately.

On the weekends, I rarely managed to watch TV on the couch without Henry kneeling in front of me, pulling my panties to the side, and burying his tongue in my pussy. And, for my part, I almost never let Henry make it to lunchtime on Saturday or Sunday without cumming, frequently having him wake up to his hard cock already in my mouth. For the first couple weeks or so, we hadn’t had the chance to truly engage in possessiveness and dominance beyond language (“tell me whose cock this is” and “I’m not letting you out of this bed until you cum in my mouth”), but we were greatly looking forward to the day that we had time for me to really give myself over to my truly dominant alter ego.

I [M] just had my first prostate orgasm in the shower and it was the most incredible experience of my life

I have always heard about how the prostate is like the male G spot and I’ve been curious for a couple years so I would try butt plugs and prostate toys, they’ve always been fun but I would never cum with them at all, I wasn’t even sure if I would ever cum like these people that make it sound so intense, to be honest I was starting to believe it wasn’t even real.

One day I was masturbating in the shower and happened to think about an encounter I had when I was around 22, I delivered pizza to a muscular man in his late 30s that towered above me at 6’ 3”. He invited me inside to put the pizza down in his kitchen while he gets his wallet to pay for it, I saw that he didn’t have a shirt on but that kind of thing happens all the time so I went in not thinking anything of it. So I walked in but to my surprise he was actually 100% butt naked, he left and came back with nothing but a towel and I couldn’t stop thinking about how much I wanted him to drop it and ask me what I thought about his cock.

A helping hand from my wife [MF]

Aware this isn’t as outrageous as some stories on here, but really enjoyed it so wanted to share.

So this week is my wife’s shark week, but being on lockdown we’ve been horny, and I’ve been helping her out a lot with her business in the evenings after finishing my own work. So last night she offered me a hand job, but also said to go put in my remote control prostate massager. I’d been edging all week so knew I wouldn’t last long. Confirmed this when I slid my prostate toy in and started dripping pre-cum on the floor. Climbed back into bed with her to find her topless. She starts holding my cock and massaging my balls but not actually stroking, whilst we kiss and i grope her massive chest (38J after breastfeeding 2 kids). Toy isn’t even on yet at this point. This continues for a while before she finally gives me a long, slow stroke all the way down, holds it there and bites my lip.