The Long Awakening

Disclaimer: All characters are over the age of 18.

1.

Fifteen years it took me to experience my first anal orgasm. I wonder how many readers will understand that, either from direct or secondary experience, and how many will flat-out refuse to believe it. But it took fifteen long and challenging years.

Beyond the first three curious years of exploring myself manually in the shower, or in bed with the lubricated fingers of a free hand as I pleasured myself the good old fashioned way, the first sex toy I used on myself I must describe with a brief anecdote.

I had been seeing Georgia for six months, up until mid-December of '11. It was the kind of doomed relationship that started as a sexual fling and went on too long despite us having little in common other than huge appetites for sex.

And I hate to say that, because it comes across as shallow, which it was. But it is what it is. We had a blazing row at a party at her friend's house a week and a half before Christmas. She told me to go fuck myself. She was done with me. January came, cold, grey, penniless and depressing, and I motivated myself to do something with the gifts I'd already had wrapped up for Georgia.

I'd donate them, I thought. But as I sat unwrapping her gifts and dumping them into a shopping bag, I nearly died inside as I visualised the potential hilarity of me donating a fucking vibrator to one of the local charities and having to explain that to them. So anyway...

In the end I did go and fuck myself.

Literally.

2.

It wasn't great, I didn't know what I was doing, it hurt like a motherfucker even with the aid of a bottle of lube I'd added to my ex's gift set. I was clueless and had received no guidance, sought no online research until after the fact. But I admit that it fuelled my curiosity all the more as time went by. It was a strange feeling that I never seemed to progress beyond, but I imagined that anal play took time to become accustomed to and to fully enjoy.

So every now and then, usually in between girlfriends, I would take some me-time and use it to explore a little further. That became a more frequent special occasion as my dating site experiences grew to include an online friendship with a thirty-nine year old redheaded trans woman, Sheila from Lancashire, who took enough of a liking to me to share her knowledge on anal play and intercourse.

When I invested in my first anal douche things became a whole lot more interesting and a lot less uncomfortable. In fact douching saw the beginnings of a whole new health kick for me. Even if I wasn't fucking myself in every position that I humanly could behind closed doors (I was), I had an extra kick in my step from that point forth, and I was growing more certain of myself as an open-minded sexual being.

Sheila, who always douched with aromatic flower water before a date, so that she could invite her male suitor to "come smell the roses," as she put it, shared much about her versatility in the bedroom because of her appreciation for eroticism, roleplay, role-reversal, and romance.

Up until that point I could only really use the advice on healthy colonic tonics, enjoying my anal self-love sessions all the more for the aphrodisiac effect of a little natural perfume. That was a turning point for me sexually. I wasn't ever the self-pampering kind. Wasn't the kind for women to pamper either.

Well, I had walked in naive but with an open mind, and left a little wiser and with a much broader mind. Sadly I lost touch with Sheila after a couple of years, but I had gotten more in touch with myself and my sexuality thanks to her so I figured that this was meant to be in its own strange way.

Still, years had passed and I still wasn't capable of reaching a prostate orgasm, as appeared to be all the rage in those days. God knows I was hitting the right spot and that I was trying different ways of hitting it, and with an arsenal of different kinds of toys.

From the clinical looking 6" wand vibrators to real-feel jelly vibes, and from one short-lived butt plug which quickly proved to be my mortal enemy to a suction-cupped 9" silicone dildo - which I got really fucking good at riding when I realised I could attach it to the side of the bath and straddle it more comfortably than the laminate wooden bedroom floor - I was experiencing all manner of strange and interesting sensations through anal sex simulation...

But after all that time I still couldn't orgasm that way!

3.

Fifteen years...

Much like how that earlier anecdote went, I had gone through another lull in my love life. It was time to do a little spring cleaning. Different apartment, different community, same story. I found a vibrator hiding on top of my wardrobe, all of the aforementioned long since gone.

I had spent four years with a woman I will not even begin to describe. I felt utterly defeated even though I was the one who'd walked that time. I did not want to think about being with another woman ever again. The last year of the relationship had left me feeling bitter in the longrun beyond the elation of finding my freedom again.

And before my libido had hit the dirt without warning and left me unable to even take care of myself for an extended period of time, I had invested in this little ergonomic prostate massager - something I'd never tried before. Their shape had always intimidated me.

Well, holy shit!

I had never experienced something so powerful. I swear, the first and last time I'd tried it I felt like I might as well had been sitting on a blender. It had been good for shits and giggles, but I had cleaned it and put it away without the intention of using it again in the foreseeable future, and I guess that's how I forgot it was there, until that day...

4.

It was early evening. I wasn't hungry. It was too hot, still twenty-five degrees celsius by 7pm. I came home from work, beelined for the bedroom and found myself retrieving the prostate massager from its little suede draw-string bag, chuckling to myself.

I pressed my finger to the standby button for a second and to my surprise it buzzed to life with a vibrant jolt. They do not make these things like they used to, I marvelled to myself. I hadn't used this thing in a year and yet it appeared fully charged.

"And why the hell not?" I thought to myself, feeling the familiar urge, the curiosity, deciding that a final opinion on the powerful little prostate massager was in order. So I grabbed my faithful douche and hit the bathroom for a deep cleanse.

5.

I had a full pot of premium anal lubricant now sitting on the study desk beside my bed, the type of lube used for fisting. Fisting had never been my idea of fun, but when I ordered it online I had imagined it would be the best kind of lubricant for ease of access and better durability. I wasn't wrong. I'd bought enough different types and brands over the years to know my way around.

I'd already had a good stretch. Now I had two thick fingers penetrating me with little resistance and I could feel the tight muscles of my anus yielding easily thanks to years of conditioning. Still, it amazed me just how tight I was after all this time.

I was barenaked with one foot up on the desktop and mindfully exploring myself just like old times, reacquainting myself with the silky-spongy bump of my prostate, my wet cavernous colon lined with fleshy ridges, pulsating, squeezing, trying to suck me in airtight.

I reached for the prostate massager and dipped it liberally into the pot, shucking off the excess drip, and then aimed for the standby button.

It had several speeds and rhythms, ranging from that intimidating full-on intense buzz to a low rumbling hum, and from a fast and eager to a sort of slow steady nudge.

I set it on a medium strength and inserted the masssager like a butt plug, still standing with one leg hitched and even standing up it seemed to fit perfectly without my muscles trying to force it back out.

I lowered my foot and tried standing still with a straight-backed posture, and ever so gently clenched my buttocks. The shock ran through my system oh so familiarly. The sweat on my brow now seemed to vibrate out of the pores in my skin.

"Fuck yeah," I whispered in the quiet solitude of my bedroom as I noted the pressure and intensity of the vibrations begin to rise up through my abdomen. I was hitting it, the exact right spot, and it felt so much different to every other time.

It felt so good in a way I had never experienced in the twelve years I had started trying penetrative self-sex with toys, but I had to work with the intensity because it was still too full-on for me to enjoy.

I lowered the massager's power to that low rumbling hum while it was still inside me, which felt deliciously baritone deep, and then opted for a medium-slow on-off rhythm. That allowed me to relax more and to become more easily accustomed to what it was trying to do to me. What I was trying to do for myself.

Automatically I added a little more pressure to the toy now ululating against my p-spot using my rectal muscles, and naturally I began to buck my hips to the sexual rhythm being emulated. And that's when the feeling transformed into something I never imagined I'd be able to feel.

6.

"Come on," I gently coaxed myself, "let it come, just let it happen," I said, pushing back my buttocks to deepen the thrusts I was now giving in to. I closed my eyes and imagined some spectral lover behind me, hands on my hips, impaling me, hitting it right where I needed it...

Hitting it...

Non-stop hitting it...

...ffffffuck me!

I've experienced orgasms that came deep from the gut and produced very powerful ejaculations, the best kind whether you're enjoying giving penetrative sex, receiving oral, or enjoying a long and lazy masturbatory fantasy.

This was not the same. To begin with I couldn't even be certain it was an orgasm. At first I started to feel like I was being expanded by some intense emotion welling up in a place I hadn't felt it before.

Imagine your hand could feel sadness. Imagine that. A part of your body that is not associated with emotion. How alien but profound would that feel? Actually that's a bad analogy. Your gut is directly tied to your emotions, and your instincts, and your mind becomes unhealthy if you don't trust your gut, or take care of it.

But I was feeling something so profoundly emotional rising up from those depths now. Stealthy at first, coming out slowly but with all certainty.

As I stood there naked, now dripping with sweat, trying to process this feeling radiating up from within me, I was becoming filled with something like a deeply buried extra sensory perception being churned and whipped into a whirlpool.

Brought to life!

My breathing, deep but growing increasingly ragged, was beginning to rise in tempo, forcing me to go shallow, and from nostrils to open mouth. My initial shakiness was becoming a steady unending tremor.

"What the hell?" I panted. My cock was only semi-erect. Virtually only a matter of seconds had passed by, not even the better part of a minute.

"This is a fucking orgasm," my mind cried out. My left hand caressed my shaven heavy testicles, pulling at the tautening skin, rolling the testes back and forth. The five fingers of my right hand encircled the thick shaft of my still-slumbering penis and began to stroke anyway.

Vrum-vrum-vrum-vrum-vrum-vrum, the massager went as my bucking hips tipped its head consistently against the bump of my special place.

"Ahhh," I gasped, again, again, willing victim to the pleasure now stabbing through my core, as the emotional and orgasmic sensation seemed to light me up from my sexual centre, right through my heart, and straight up into my consciousness.

I was really orgasming. Not cumming. Not blowing my load. I was orgasming from my anus and right through my body and the feeling would not stop. Like a female orgasm? Closest thing to it I can imagine.

Hallefuckinglujah! Divine providence had come!

My mind seemed to fragment as I struggled to hold all of my thoughts, emotions, and sensations together. I suddenly found myself laughing, shouting aloud like a madman, "HOLY FUCK, YES!!! YES!!! HIT IT, HIT IT!!!"

My cock still wasn't completely hard and now the sensations were becoming too much to control. I couldn't hold back. I was dripping pre-cum like never in my life. I panicked and bent over to pick up the waste paper basket, not daring to run for the bathroom and lose the feeling. The feeling instead flushed right through me and before I could take aim the walls in the dam began to break.

It was the feeling of two separate orgasms becoming as one, a one-man chorus of sexual release. I spurted from my semi-erection, and Christ it was a lot. It splashed against my protective hand and exploded all over me. I was half-laughing, half-moaning, revelling in my premature release, my libido dormant for too long before this moment.

I didn't care in the moment that I hadn't had the time to get hard. Again and again I ejaculated thick white globs, splashing in an arc down all over the bed spread and the laminate floor. And after I pulled out the prostate massager with a slick pop, I slicked back the sweat from my face with my forearm, breathless and in total disbelief...

Fifteen fucking years! That's a long time for such profound feelings to be bottled up inside.

Afterword:

That night I must have masturbated three more times. My dick was harder than it had been in so long. The first time I ejaculated prematurely once more. And the volume of semen I ejected had been almost as great as before.

I then felt a sudden urge to go to the bathroom. To my shock and embarrassment I didn't make it in time. I pulled down my boxer briefs as I sat on the toilet and reluctantly surveyed the damage. To my grim fascination I had passed a pale, almost clear substance. I know it wasn't lubricant. I'd used just enough to get the job done, not enough to make even the slightest mess.

I'd heard or read somewhere once that the prostate could do that when milked. Totally forgot about it since it had never happened to me. I showered and went to bed and pleasured myself again two more times before dawn, the real life possibilities now presenting themselves as peak masturbatory material for an imagination running wild.

I hadn't been that horny in so many years either. It really got me wondering if somebody else could evoke those same combined sensations and emotions within me, given the chance to come slide it in and bump up against my prostate.

I was wide open to the possibility after that day.