My Anal Journey.

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So I want to preface this by saying I’m a 29 year old bisexual man who is happily partnered with a wonderful girlfriend who is well aware of my orientation and play.

Also sorry in advance for the text wall but there’s a lot of stuff to cover!

Anyway, let’s start. My butt is still basically virgin – many years ago I let one guy with an absolute monster of a dick enter my ass and that was… a mixed bag. He was this older guy who lived up to certain stereotypes and mee being me I wondered I could brave my way around him beautiful but humongous cock. He stretched me to breaking point and we had to stop fairly quickly (in hindsight I should have built up to a dick that size and we should’ve had more than a thimble of lube handy). I bring this up because there’s something that I remember clearly: even though I was in agony (he even ripped me slightly I found out the next day, big ouch) there was a point while he was inside me where I felt that glistening cock tip hit something wonderful. It still blows my mind that even through all that pain (a level of pain I’ll never want to feel again) when his thick ebony dick got as deep as it could I felt a deep throb of pleasure as my prostate was pushed towards my balls. Like honestly, when his veiny cock hit that place it was a feeling so intense it had me drooling out ragged breaths into his pillows while our bodies lathered with sweat on that hot summers night. It was a night of firsts for me and even though I had to stop the anal stuff, I hungrily and nevously ate his delicous ass while I stroked his cock – but I digress – I’ll move on with my story because if I think on this 10 year old memory too much I’ll definitely get too horny to type.

Anyway, my arse has been completely unexplored this last decade so has snapped back to its original tightness – I’m a viking looking guy with very long hair, broad shoulders and I spend my life on my feet so I’ve got a big juicy butt from constant walking. Recently my partner and I decided to buy some toys for the first time and in my heart of hearts I knew what I wanted but I was too frightened to say. Luckily she’s great and said “what about a plug for you?” So my thirsty bi ass could barely contain my excitement – remembering that night where that gentleman took me and wrecked me, his enormous black dick hitting my g-spot while my precum trickled over his bedding. I wanted to get that prostate stimulation again – I’m not so into the idea of being fucked but I’d do *anything* to give myself a more powerful, intense orgasm and experience that sensation again.

So the butt plug comes, it’s 3.5″ and has a load of vibrate settings – my heart is in my throat and my chest pounds as the postman hands it over. My girlfriend is at work at this point so like the hungry little cock goblin I am, the lube and plug are out of their packaging in under two minutes and I’m stood in front of the mirror upstairs looking at my uncut dick twitching in midair. This was my moment to get my prostate vibrating against my balls again, I was gonna have the best orgasm ever so I lube the toy up, whack it on the highest vibrate setting, struggle it into my tight butt and… so what. I have a fairly typical orgasm and hardly feel a thing. I’m left feeling dejected with all I have to show for my efforts are sticky, lubey fingers and a sore arsehole. I was devastated and sad – me and my partner have sex nowhere near as often as I’d like so this dirty playtime was hugely crucial to me and it was just so average. For a weeks I give up on the idea until a couple of separate days recently when I finally got it right…

I realised I’d been focusing on things wrong – the goal here wasn’t just the orgasm but the overall pleasure. Apart from the butt stuff I’m also mad into edging. I began to play with myself in the spare room extremely slowly, I was butt naked lying on a towel and working my hard dick until my balls were tight against me from the toe-curling pleasure. With my free hand I stroked a gentle ring around the rim of my hole, making sure it is absolutely glistening with lube. It caught me off guard how easily my finger slid in… I let out a gasp and chuckle which made my anus clench and sent another jolt through my system making my cock bounce around more. I’m even more surprised when the second finger slides in and I’m suddenly feeling full and flustered. By this point I’d edged several times and I was so sensitive that even stroking my nipples made me twitch. It was time for the plug. Like an orgasm-starved lunatic I started feverishly pumping lube onto my butthole and wanking it over the plug. I slide the plug in and wait a moment, gripping my cock with both hands, hands that are absolutely soaked. I switch the plug onto its highest setting and it is like my whole body is electrified, there’s only so much more edging I can take. My legs were in the air and I was gasping and grunting like I was absolutely railing someone and with the amount of lube that was covering my hands – it didn’t feel too far off someone’s hole. Then I came, I absolutely exploded, the last thing I remember is trying to edge but repeatedly screaming “I can’t stop” as my back tried to snap in two, my eyes rolled into my brain and I absolutely paint my lower body with these heavy spatterings of hot cum. I’d convulsed so much as I came that the wet plug actually slid out of my arse and onto the towel leaving me a gibbering, soaked mess of a person. I’d gotten so dirty and worked up that all I could do is rub myself against the towel as I felt lube trickle out of my body. I was so exhausted all I couldn’t even bring myself to get up for twenty minutes so i had to mop my jizz up with my boxers. The boxers were actually in such a state that they gave me thoughts about selling them in the future when I’ve had a session like this.

So there you have it, a story of how playing with my ass left me a husk of a man. The thing is… I know the plug isn’t or is barely even hitting my g-spot… I’m gonna train my tight booty a while longer and work my way towards a dedicated prostate stimulator. If my orgasm was this intense just from the plug… I can not imagine where it’ll go in the future but I’m excited to figure out!

If you read all this, I hope you got a dirty thrill.

NSFW: yes

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