Playing with my Prostate Opens up a new World of Pleasure for Me [M] [Anal] [Prostate Stimulation] [Masturbation]

This is based on a true story of how I discovered the pleasure of prostate play. Most of the details really happened, with some small changes made for the purposes of storytelling.

My name is Jack; I’m in college in my early 20s, and would definitely consider myself a straight guy. I never really had any success dating women in college, not for lack of trying. I did, however, experiment a lot by myself. One day when I was jacking off to porn, I discovered “femdom” porn.

It was a video of a man who was tied down to a bed, with the dominant woman riding him reverse cowgirl, hard. She wore latex high heel boots, fishnets, and a corset. Her breasts were bouncing rapidly up and down while she fucked his brains out. And all he could do was squirm and moan while he was tied down to the bed. He was nothing more than a toy, useful to her only for her pleasure.

24 [M4F] #Netherlands Anal Training & Prostate Milking

 

#Why anal training?
*“Anal training serves several purposes which are not only essential for your success, his emotional well-being but his health as well. Anal Training can also be referred to as prostate milking although in our case will be called anal training because is more than just prostate milking. Anal training is a necessity if your male is locked up for a week or more otherwise his prostate can get clogged up and his chances of getting prostate cancer increase. Milking not only causes a release of semen clearing out the prostrate but, will provide him with none of the satisfaction of a regular male orgasm. A male is usually even more frustrated after a milking than before because he has been stimulated similar to an orgasm but not allowed to have it. However, over time he will relax and the feeling of frustration will disappear. Milking also helps to prevent nocturnal or spontaneous orgasms which can happen if he is locked up long enough without being milked or allowed to cum. You can look at prostate milking through anal penetration or prostate stimulation as a necessary procedure. When you penetrate your hubby, you must not release him from his device or he may be tempted to stimulate his penis and all of your hard work up to that time will be ruined.*

I [M] just edged for over two hours. I’ve never felt so incredible.

I’m still in shock, but the title says what it says. I’ve never done something like this. I can be a bit indulgent, but I’ve never even come *close* to this. I hope you enjoy reading about my experience almost as much as I loved having it. For reference, I’m a man in my late twenties, about 5’9″, pretty fit, with a cock that’s just above average. And I am a hedonist.

I have a really simple morning planned out. My partner will leave for work a little after 8:00, then I’ll have a smoke, play a game, and treat myself to a nice long edging session with my prostate massager (I figured 30 minutes, tops) before logging onto my work laptop around 10:00. It’s going to be an easy day anyways. I feel the weed pleasantly cloud my brain a little as I finish my first game, and I’m getting really horny. I decide to switch gears — jerk off now, and maybe play one more game before work. I take another deep hit from my vape and start to feel a dull emptiness in my ass. It’s that ecstatic ache that grows more intense as you get harder. I’m chasing that feeling of being lost in sensations, and of being blissfully *full*. As I slide my toy into my ass and sink into my chair, my mind starts sinking into hedonistic lust.

A Super Sexy Sunday [MF]

Hello gw stories! I have posted here before but it was so long ago I can’t remember the login for that account so I created a new one (and waited the required period) to share this story with you all – it was just that good.

I (38M) had the sexiest Sunday in a very long time with my sexy (40F) wife just a couple of days ago. I am still thinking about it and getting hard, so I thought I’d get it all out so I can experience it over and over again.

Rachel and I have been married for 15 years, and have 4 kids – so – it’s a busy household and pretty chaotic most of the time. Plus my wife deals with depression and anxiety, so intimacy is not always on par with where I’d like it to be. If I had it my way, we’d be doing it every day – but she’s more a once-a-week kinda gal.

It had been over a week and I was **horny** with a capital **H**. We started the morning with some deep kissing in bed but couldn’t go any further because – sigh – *responsibilities*. But later in the morning she kissed me and looked in my eyes and said “let’s have a sexy night.” I had no idea what lay in store, but knew it would be *good*.

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.