Hitting It

Author's Note:

This is a follow-up to my debut short, 'The Long Awakening,' which can be found in the Anal category here at Literotica. You can read them in whatever order you like. It's only fair since I write what I like.

Disclaimer: all characters are over the age of 18.

1.

Suffice to say I put my trusty prostate massager to good use a few more times since finally experiencing my first anal orgasm on that fateful hot sticky evening. I couldn't guess the number of times I've fucked myself since curiosity first got the better of me all those years ago, or the number of artificial phalluses I gladly accommodated along the way, but regarding the former, we're definitely in the hundreds by now.

Fifteen years chasing a fleeting but magic and unforgettable moment, an immense and life-changing event consigned to the secretive shadows of unspoken personal experience. It was not something I would be capable of keeping to myself.

I would want to share it with somebody sooner or later, which is why I chose to write about it - to get the ball rolling!

Since that day and also since I documented the experience, emphasizing the emotional impact of what it was to become so aroused and orgasmic through prostate stimulation, I encountered similarly intense orgasms, though no act of self-love since had quite the same level of emotional impact.

One seemingly simple question answered, regarding my breakthrough, had led to a slew of burning questions that needed answering in order for this journey of self-discovery to continue to another.

Looking back as I acknowledge the changes I have since gone through in life, I have to acknowledge again that something huge had been botttled up inside me for so long that maybe it contributed to me being repressed in some way.

2.

A little nugget of truth about me that I don't recall having shared with you yet. I have experienced depression and anxiety on and off for the better part of my adult life. The numbness and emotional unavailability resulting from that has had an effect on my libido a number of times. Maybe more importantly it has negatively affected all of my relationships.

After the last one ended, I was dead in the water for so long that I thought it was over for me, that not only would I end up compeletely loveless, but sexless too. My personal sexual breakthrough not only proved that not to be the case, but also reminded me that I was hiding another side to myself despite having accepted that I was not completely heterosexual.

Numb! That was what I had felt for so long until the evening I impusively took pleasure from massaging myself to anal climax. Two weeks later I was struggling emotionally with a number of things but functioning nonetheless.

But over the course of maybe three or four days I found myself more and more just wanting to cry. I hadn't been emotional this way for so long that I have nothing to compare it to. A number of days I was out in public and feeling generally fine within myself, and then out of nowhere, with no automatic thoughts to examine, I was welling up and fighting the urge to burst into tears.

A couple times I was lucky enough to be by a local park or alone on a footpath, and I allowed myself to submit to these emotions, but it was as if my mind and body were of two separate beings. No automatic thoughts gave me no reason for wanting to cry.

I was being hormonal, experiencing a physical-emotional outpouring. And since I am documenting these facts, I cannot withhold the fact that since this awakening was not all at once in occurrence - instead happening day by day as my dynamic with the world seemed to be recalibrating one person at a time - I felt, for the roughest of days, that I could die rather than go through such a turbulent emotional awakening all over again.

Well, I came to the conclusion in the midst of this trickling emotional stream that it was something to be embraced, not fought. Here within me was an awakening after all. Man can choose how he lives but not how he becomes alive.

I might have walked the path to this awakening, and to be awake is to be conscious, and to be conscious is to act. But the impulse is what drives and directs the avatar and I cannot speak for the nerve that I touched that seemed to result in my own awakening.

Neither can I speak for why our eyes see life so differently when one moment in time seems to reset the way we feel about it and compelely change the path ahead.

I could have chosen to answer other questions; Am I gay or bisexual? Am I just all the more screwed up from tampering with my own biology? Or was I like a ball of string all along, all tangled and knotted in life beyond my intended function, until the long anticipated orgasm that shook loose that one vital thread?

Other questions instead demanded priority: What was I going to do about it? Should I continue to follow the path of least resistance in life or would this stream of consciousness lead nowhere if I didn't fight to direct it?

I was confused, in case you haven't figure that out. God, that realisation was probably more profound than it should have been, but it made for a hearty laugh. I was confused, thinking too deeply into it for the lack of doing, socially.

3.

Her name was Ramona. She wasn't new to the area. She was a frequent and familiar face where my friends and I would hang out, a little suburban retail and recreational sprawl, pretty much a row of local shops and houses surrounding lush community gardens.

We barely crossed paths with Ramona and her friends, as in stopped to talk, but just to project the fact that we were friendly we had grown to say hi in passing and to acknowledge each other over time.

People would stop and talk about her, seeing that I actively spoke to them, and I'm guessing they thought that I knew anything about her. They'd come up to me and ask "What's going on with them?" with a telltale fingertap to the head.

"What's the world coming to? I just don't understand..."

It got to a point where I'd boiled my response down to, "If you're not in somebody's life there's nothing really to understand."

One night my friends and I were out on the street, sharing a smoke and loitering around the edge of the gardens. We heard the telltale sounds of Ramona and her friends talking loudly from halfway up the street, on the edge of the greater residential area.

I'd fixated on them as Raj, Lily and Rita were gossiping, and saw Ramona and her friends go suddenly quiet as they passed a drunk group of teens who had already passed us by with palpable sulk and angst. As is usually the case I assumed nothing was going on, but I continued to watch because my gut instinct wasn't yet decided.

When Ramona and her friends passed the other group, heads turned, something was said, and the girls kept walking, Ramona turning to ask, "What?"

Not another word was said. But the lads weren't walking on. They'd stopped to watch as had I, but then as the girls walked in our direction, so did the boys, no more than a block's distance between them. I now trusted my gut and waved over to Ramona and her friends, telling them to come over.

They didn't ask, just came right over, and under my breath I told them to sit amongst my friends on the benches. Either the lads following would see us and change their minds about what they thought was going to happen, or, no...

They kept coming towards us. "Just play it down a minute," I suggested and relit my joint. And as they came upon us, I just blew smoke and stared right through them as I had when they came from the opposite way.

All sulk and angst, but no guts. Not even the instinct to tell them that they were about to take a fucking beating. My joint half smoked, I passed it in front of Ramona's face, and she reached out and took it, a steely glare as she stared back into the face of the lad staring right back at her.

And let me tell you, there's nothing quite as unpleasant as feeling adrenaline and bone-deep apprehension clash under the cloud of a weed high, knowing that you're inches away from going at it with a gang of kids and knowing all the more that your reflexes are going to be miles off.

Oddly I felt serene, still as a statue, coldblooded as a snake. My heart was still enough for me to still hear the summer breeze as nobody around me spoke, until Raj asked, "Lads, what are you looking for?"

And there went my cool.

4.

For two days Raj wouldn't answer my messages. He spent thosw two days off work, licking his wounds, drinking the pain away. Neither Rita nor Lily had gotten through to him either. He was embarrassed that he'd taken a fat lip from some weedy 18 year old after tripping on his own feet and ending up on the floor. That same kid got knocked down and kicked unconscious by four girls.

Apart from biting the inside of my own lip and ending up with somebody's bite marks to the sharp corners of both elbows, and a little swelling to one cheek, I was fine. Apart from now being in permanent fight mode, expecting a repeat every other night on that same stretch of road, I was fine.

So I had gone out looking to mark my territory on the neighbourhood as rumour spread like fire that those lads had gone looking to fight a bunch of girls. I bumped into Ramona and one of her friends, Samantha, on a breezy summer evening, and before I could say anything they started inspecting me for wounds, asking if I'd been hurt.

She and Sam told me that their other friend Kayleigh knew one of the lads. As a result they were all down at the cop shop having big scary words such as Transphobia and Hate Crime thrown at them.

"Oh dear," had been my tickled response. They'd gotten the shit kicked out of them by two unknown adult males, then by five girls, and now this? It couldn't have happened to nicer people.

"Listen, don't be shy, okay," I told Ramona, "come over and chat with us whenever you feel like it."

I didn't expect her to ask for my phone number, but that's pretty much where we started to talk between just the two of us.

5.

I should describe Ramona. On my travels around Norway and Scandinavia I've met countless women with the same strong but beautiful features. The subtle but strongly set female jaw, sharp brow, high cheekbones, the sensuous but sharp lips that could have been drawn by an artist with a fetish for warrior women. Only the finely schiselled nose didn't stand out as typically feminine, but the amber doe eyes balanced it.

She had all that and a body firmly placed between athletic and soft. She bore an impressive washboard tummy that practically mocked most of the women on the street. She wore silky chestnut hair down to the middle of a long and slender neck, which suited her pale smooth skin.

She was barely a B-cup and therefore beneath the sporty crop tops opted to go sans bra, nipples for days, rather like our friend Rita. The other feature I found myself fixated on was her high up bubble-butt, which practically popped out of her loose, low-cut cargo pants.

Now Raj, poor Raj who suffers life almost as easily as I do, has seen me with nearly every woman he knows on my arm throughout the years we've known each other, and wondered what the hell is going on. The look on his face is always comical.

I don't date on my own doorstep. I'm just not a dog who chases everything that lets him within sniffing distance. Women feel safe around me, which is one of my great compliments in life. For the most part I just enjoy the company, and the shade thrown at me by men fitter than me, men with money, men who throw about an alpha type of mentality like that gives them priority over all else.

And sometimes the look on other women's faces is just as priceless, because I know how they regard each other. Everything is a competition, even how low a woman can go to get what they want. In that sense, men and women are no different to me.

I am michievous at heart, so the idea of Ramona on my arm in public excited me when she texted to ask me what I was doing one boring afternoon. I wanted to go shopping for some new underwear and some stuff for my kitchen, so I invited her to go with me to the TK Maxx up in the neighbouring borough's retail estate.

We waited for the train. I noted how many people would stare at us as we chatted and boiled it down to a percentage. We stood on the train for the two stops it took to get there and chatted some more, and I did the same. We walked the rest of the way, past Subway, McDonalds, KFC, Starbucks, and I was in two minds the whole time - playing it casual with Ramona, being carefully curious, and all the while counting the stares.

Bearing in mind that I get a lot of stares on my own, for whatever reason, I knew it wasn't the same thing, but I had always been self-conscious when I was young. It took years for me to relax and not care about it. If anyone had a problem they could come over and make a fool of themselves.

I still couldn't put it out of my mind though. Ramona was undeniably feminine, and as I'd already said maybe more than once, she was strikingly feminine.

Pretty.

We were crossing the huge expanse of the car park at the retail estate and whoever planned that place wasn't a fan of pedestrians. It was busy and cars weren't all driving at respectful speeds. My anxiety was coming up, but instead of letting it get to me and injure myself rubber-necking, I smirked and held out my hand to Ramona, prompting, "come on!"

She put her hand in mine, I squeezed it and jogged her across the last stretch of road, weaving in between the cars backing up and beeping at each other. And when the automatic doors to the store parted before us, we didn't part too. Her hand stayed in mine for as long as I let it.

6.

"What do you think?" I asked. We had mulled over to the men's underwear section after casually zigzagging through the soaps and perfumes and the men's and women's clothes. I held up the pack of all-black New Balance boxers, as modelled by the unrealistically muscular body printed onto the front of the box.

"I look nothing like this, obviously," I said dismissively.

Ramona came over, cocked her head in consideration, and anchored the corners of her closed lips downward. Then she nodded. "They'd suit you."

I clung to them, bore the price tag in mind, and lost myself in thought for a moment. "These would go better with your tan, and your bum," she then said, which broke me out of my reverie. She'd been looking, huh?

I looked to her, in her hand she held up a pack of blue Adidas boxer briefs. They looked skimpier than what I was used to. Microfibre too, the stuff that's so thin and weightless that it feels like wearing nothing.

"They could be small enough for you to wear," I joked, wondering what she would say to that.

"How do you know what I wear?" she said with a playful smile and held my gaze.

"I don't know. You show all hips and I've still not seen a hint of underwear, so I'm guessing something skimpy."

"Maybe I don't wear any..."

I held that gaze as long as it would last. I wasn't one to quit flirting, even if flirtation hadn't been my intention. "Yes you do, you put too much effort into your looks not to," I hazarded my guess.

Ramona blushed and looked away to hide what looked like a tight-lipped smirk. I threw back the pack in my hands and coaxed the Adidas' from her hands, grinning. "I'll try these, thanks," I said, and we moved on deeper into the store, making small talk.

Back home we parted ways again. This has happened so many times with women too, I don't always know what's comfortable or whether I'm overstepping boundaries. I figured Ramona trusted me and liked me and I'd gauged that she wasn't shy or detached otherwise she wouldn't have held my hand that day. But I didn't want to come across as grabby.

Did I kiss her on the cheek? Did I hug her? Obviously not a handshake, for fuck's sake!

"That was fun," I admitted, beaming a big smile at her, happy to have one in return. We were still just about walking side by side to my gate, so casually I put a hand around her waist and gave her a friendly tug toward me so that she bumped into my side.

I didn't expect that she would meet the gesture with an affectionate pat on my bottom, but there it was. I didn't entirely expect to feel the cock tucked to the side of my thigh twitch and grow either.

"Text me to let me know you got home safe," I said and we parted ways.

7.

"You're not out tonight?" she texted me some five hours later. It was near ten in the evening.

I'd been part way through an erotic short story on Lit. I was a little high too, and enjoying losing myself in the moment listening to some vaporwave.

"Nah, having a little me-time tonight. You?"

"Me-time is good," she replied with a smiley emoji. "Nah I'm just bored, wandering with my girls. How are the new shorts?"

And a wink.

"How do you know I'm wearing shorts?"

Counter-wink, bitches!

"Oh so it's that kind of me-time!"

I didn't know what to say to that. I rememeber sitting there... yes, naked... mostly because it was a sweltering hot night... with the fan on full-blast... but yes also, I was hard because I had already been aroused before we started flirting again.

"Lol the shorts are great, actually they're pretty damn sexy," I recalibrated, hoping not to come across as too much of a flirt, and failing all the same...

X.

8.

The next couple of times I spent time hanging with Ramona, my friends were all off doing their own things. Namely Raj was always sleeping, Lily was banging Raj's cousin Kamal, and Rita was being her usual social butterfly self.

So I got to know Ramona's friends a bit better. Samantha, who just so happened to be Ramona's first girlfriend years ago, which was a twist I hadn't seen coming, and Kayleigh, who was just Kayleigh - what you saw was what you got.

We hit another local park further out of the way, a great sprawl of field and trees with a little access road in and out. We lugged some beer down with us and picked a bench near one of the access road's streetlights so we weren't sitting in complete darkness by the time the last of the day's light was gone.

It was a relaxing time, we had a good laugh, but I couldn't help but notice that Samantha kept giving me this knowing look whenever the conversation picked up between me and Ramona.

Time came that I had to go pee. I wandered off to a bush maybe ten yards away and on the way back the larger silhouette of one of the girls approached me. It was Samantha.

"Hey," she whispered, "listen, thanks for being cool with Ramona..."

I was feeling the buzz of more than just beer, and feeling very agreeable. "Not at all, she's lovely!"

"Listen, she doesn't get to make many friends," Sam danced around the context with a bladderful. "People are mean, you know?"

"Yes they can be, and that's their loss," I told her. "You must be a great friend to have," I then said, recounting what I now knew. "After the coming out and the transition and everything you're still there no matter what."

"I'd do everything for her," Sam said and meant every word, I believed. "But don't think I haven't seen what you're doing..."

I almost reeled, but I felt zero need to defend myself. "I don't know what you mean," I whispered into the shadows.

"No no, don't take it the wrong way," Sam disarmed. "Nothing's brought her out of her shell like you have lately, that's all I mean. Be careful."

"Sam, I don't know what to say to that. Do you mean what I think you mean?"

Despite the surrounding darkness, my keen eyes made out a shadow of a smile. "She proper fancies you," she said in a playful tone, singing it like a playground taunt under her breath.

Actually that made me feel great about myself.

Elated.

Energised.

Risqué.

I went back to join the other girls, specifically to sit next to Ramona. The timing was in no way coincidental. As I sat and studied Ramona's face, adorned with shades of streetlight and the patterns of the leaves of the tree above us, Samantha called out to Kayleigh, cried for her help from behind the bushes.