Hitting It

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What the hell was I doing? I was in my early thirties. Ramona was 21. But upon the moment of truth there was no denying the growing chemistry, the prolonged looks, the growing mutual attraction..

Yeah! The fact that I found her pretty and would be more than willing to explore that avenue.

Kayleigh got up off the grass, dusted herself down, and disappeared into the night in search of Sam, calling back to her, playing lost.

I smiled warmly at Ramona, gazed into her eyes. Our faces were only a foot apart...

9.

"Hey lovely," I typed "what are you up to?"

X.

Sent.

It had been maybe two hours since I'd last texted Ramona, flirted outrageously with her.

"Having a little me-time, you?"

xx.

"Not tonight lol...

"Forgot to charge up my stuff," I added with baited breath, throwing that secret out there in all faith that it'd stay between the two of us.

"Ooh, what kind of stuff?"

There it came, the key question, and the moment of truth.

So I told her about my prostate massager. The conversation quickly became all about it. It became an emotional outpouring of my soul. I physically couldn't hold back. I told her everything, came clean, and braced myself for the rug to be pulled out from under my feet.

"You're cute," she responded with a big purple heart.

"Nothing on you," I fired back post-haste.

"I disagree, you're sexy!" Another heart.

"I agree, thanks," I replied mischievously.

"Hahaha just going to leave it at that?"

"No," my reply came a couple of minutes later, with a photo of my butt encased in snug blue boxer briefs.

"That's going in my spank bank," Ramona texted back.

Wink.

"You like?"

"I would totally fuck you."

10.

There was no denying how I now felt. How she now felt. We had met a couple more times, spent time around each other with friends in the mix. That should have been awkward but I think the top and bottom of it was that I just didn't care what people thought. And from what I could gauge, either nobody noticed any dynamic change. They certainly didn't ask questions or confront me about it.

The next Friday that came around I took a deep breath, looked left to the last fifteen years, and then looked right to what was right in front of me. And then I crossed that stream of consciousness into unchartered waters.

Nervous didn't even begin to touch on what I felt. Impulse lit me like a live wire, had me thrumming with an energy I didn't know existed. I texted Ramona in the mid-afternoon and asked where she was. We met in the gardens where we usually hung out. I hugged her gently and planted a kiss on her cheek.

We were all smiles and knowing looks. People watched. My hands held her in place by her hips, and before she could ask me anything, I had to put it out there.

"If you're not doing anything else tonight, would you like me to take you out on a date?"

Ramona's eyes lit up. I had never seen a girl blush so hard. Instead of looking away like she always did when something made her shy, she didn't take her eyes off me when she accepted.

"Okay," she beamed. It was almost a question rather than an answer, so I took the lead.

"Dinner, new Nic Cage horror movie at the Odeon, and then drinks?"

"Deal, yeah... I'd like that," Ramona nodded, blushing a little harder.

11.

22:35 came, the lights of the screening room faded back on. We were breathing fast and shallow, blushing furiously, grinned at each other like teens as we licked the taste of each other's lips from our own.

We stood up unsteadily, roasting in our skins, and beelined for the bathrooms to refresh ourselves. After that we walked arm in arm out into the darkening evening. The intended bar where I would take Ramona for drinks looked so far away, on the opposite end of the estate.

I kissed her on the cheek again, closer to the corner of her lips. It was intended as nothing other than affectiionate despite how we were clearly now feeling about each other.

"Shall we go get a drink then?" I beckoned, looking to her, studying her as the cogs visibly turned. God almighty, I could feel her deep down in my gut. My instinct was in overdrive and I needed to cool off.

She took my hand, squeezed it and looked me square in the eyes. In that moment the magnetism became impossibly stronger. Ramona then moved her lips past mine, reached up to my ear and whispered, "one for courage?"

12.

We kissed outside the bar. We kissed in the back seat of the taxi where half the way home she took my hand and placed it on the inside of her thigh. I felt a throbbing hardness as girthy as my own, and I squeezed it, rubbed it, gave in to want and to the role that I was soon destined to take.

And we kissed at the doorway to my apartment building, kissed outside my door, kissed in the dark of the hallway, slowly undressed, licked, sucked, tasted each other.

I led her by the hand into my bedroom, sat her down on the bed, kissed her again, and left her to set up the sound system and the blue and pink neon lights I had set up all around the room. I handed her a ready-rolled joint and warned her not to get too carried away while I went to the bathroom to freshen myself up.

In the boiler cabinet behind the shower I'd hid my essentials, had prepped for the evening already, so I didn't take so long to be completely ready for Ramona, 100% certain of myself.

I was beyond excited, filled with as much determination as I was with nerves. When I returned to her I first saw so much glowing neon flesh, naked and anticipating. All that remained was a little black satin thong, with a big bulge...

Too big a bulge to remain concealed!

Well here I was, stood in the doorway, in total adoration of her, jaw hung slack, and eyes no doubt filled with lust's dark and brooding fire. In nothing but my tight little blue boxer briefs.

I crawled onto the bed, pawed my way up beside her body so that all of this naked flesh touched tantalisingly upon flesh, and as I held her close to me, we shared smoke.

Next thing we were kissing each other all over. Peeling off each other's clothing, freeing the hardness, handling each other seducltively.

And it was as though I'd done this a hundred times before - we licked and sucked each other's cocks in a dangerously close game of edging, almost daring each other to cum but needing more than that.

We kissed as the high levelled out, a little closer to midnight, tasting each other on our lips and tongues, caressing each other while crossing swords and grinding into one another.

That was when Ramona parted lips with me and shot me a devilish smirk, her eyes as black and brilliant as tourmeline in the sultry glow of the encroaching night.

"Do you want to put a condom on me or..."

I smiled, bartering for time. I hadn't thought about that. My stomach was doing somersaults. I'd been so preoccupied, not at least with the fact that my world was about to completely change, that this tiny fact of the real reality had completely thrown me off.

"I guess I should, shouldn't I?"

"Well, I'm virtually about to take your virginity," Ramona reasoned, "and there's only one thing you'd get from me..."

My arousal nearly had me cumming hands free by this point.

"Do you want to use protection anyway, or do you want me to fill you with my cum?"

I held close to her, rolled her over onto her back, and inched my way slightly down her body until I was face to face with her pointed pink nipples. Seductively I sucked one after the other into my mouth and licked my way around her aerolae.

Meanwhile one hand searched the desk at the side of the bed, top drawer, front left corner. I grabbed the pot of anal lubricant and popped the top, placing it on the corner of the desktop right beside us.

"Cum in me, please," I said and it was my turn to blush. Ramona lurched forward, playfully snaked her tongue into my mouth. "Yes baby."

13.

Fifteen years...

At first I talked about how the wait was worth the orgasm. That was just me, learning to accept myself, unbottle the deepest truth. Well, that wasn't all of the truth. It was maybe a taste. Because when I finally experienced being given penetrative sex by a loving partner, a beautiful kind of creature I'd never fully considered embracing before, the man inside of me came out a little more into the light of truth.

One day not so long ago I had stood at the side of my bed, leg up on the desktop, slipping a prostate massager deep into my anal cavity. Ramona in her wisdom figured that the best way to do this was by a game of comparisons.

Her thick, long uncut cock didn't meet a great deal of resistance, as she slid up behind me and I told her not to worry about being too gentle. Once the head popped in her endowment seemed to spill right into me to fill me up.

And with those hands coming to rest on my hips, as though I was now the woman in all of this, I could happily allow her to guide my movements as we began to slide together.

Both feet planted firmly on the floor next I started to buck my hips, giving her backshots, fully accustomed to her very real flesh and blood, and leaned forward while placing my arms behind my back.

"You were born for this, weren't you, baby?" she gasped as the bulbous head of her cock now juiced up my prostate. She had a stronghold on my forearms, her hips clapping hard and fast against the cushioning flesh of my butt.

Christ, that feeling was coming up out of me again, that magical emotional orgasm rising from a physically impossible depth, building up in me as Ramona expertly nudged my sweetest spot into a frenzy.

"You have no idea what this is doing to me," I sobbed in between moans, trying my best to clap back in sync.

"Does it feel good?"

As if my own cock being so hard and upright that it threatened to kick me in the gut with every thrust wasn't telltale enough!

"I feel like I've been cumming already the past two minutes," I gasped.

"Mmmmm," Ramona groaned, pulling me back into her and sucking hard on the kink between my neck and shoulder, and she thrust slowly as deep as I could accommodate. In the same movement she reached around and wrapped her hand around my straining erection and began to slowly masturbate me.

She whispered hoarsely and with hot breath into my ear, "I'd love to fuck you on your back so I can watch you cum, baby."

Before I knew it I was eagerly lying back, propping a pillow under my lower back, and edging myself to the end of the bed, pulling the soles of my feet together and tucking my knees back.

Seeing Ramona stand firmly between my legs in that moment, a picture of utmost erotic femininity towering over me, nearly sent me over the edge once again.

Seeing her take hold of her glistening hard cock, which had already transformed me into a sexual receiver of inexpressible orgasmic pleasure, and lower herself so that I could see her sex aligning with mine - I couldn't contain myself!

I felt the slippery head kiss my rosebud. She dipped three fingers into the pot, slathered more of the anal lubricant over her cock and my pussy and looked me in the eye with an irresistibly coy smile.

"You can say no, but I need to ask you something..."

"Yes!"

Ramona giggled. "I want to call you daddy."

"Yes babygirl," I sobbed needily. "Do it!"

Her eyes rolled up white as we melted together that last time. Again I was full, then empty, then full, empty... being driven to a mad-minded kind of euphoria. The orgasmic feeling hadn't even left me, just feigned dormancy. Now it was spreading through me like wildfire.

Now as Ramona gripped my ankles, spread me wide, and began to fuck me with slow and deep strokes, she began to cry out in ragged breaths, "oh god, yes daddy... let it all out, let it come..."

I grabbed the shaft of my straining cock and frantically started to masturbate myself, embracing the beautiful vulnerability of this love. "Oh god, Ramona," I suddenly sobbed, overcome with emotions I'd never felt in my life.

I almost couldn't breathe. Tears streamed hot and salty down my cheeks, my heart felt fit to burst, and all I could do was cry her name. Still inside of me we crawled into the middle of the bed, face to face, and she was now holding me, telling me it was okay.

"I never thought I could feel this," I cried against her neck, my arms and legs wrapped around her.

"Feels good," she spoke with her soft lips against my ear.

"Feels right with you," I responded weakly, my hands caressing their way down her back until they rested on her smooth round muscular buttocks. And I began to coax her movements once again, feeling that delicious slippery suction between us come back into play.

Ramona searched my eyes. I searched hers. She asked me if I was ready to cum, to really cum. I guess my face said it all. She leaned back onto her knees and repositioned my legs, placing the bare soles of my feet onto her breasts, and began to fuck me at a seductive speed, building steam as she went.

He breathing ragged once more, my eyes widened to the realisation that deep inside of me I could feel her expanding outward, stretching me around her all the more as the moment of irreversibility approached. My hand wrapped around my thick veiny cock was a blur in that moment.

And then something else I hadn't truly anticipated happened. The thing that I now felt as though I had wanted all of my life. Sat right in front of me, saddled inside of me, hitting it, hitting it...

Hitting it so fucking good!

Her beautiful face, somehow both frantic with desire and yet as serene as a leaf falling from a tree on a windless Autummn day, conveyed to me her deepest gratitude-

Her love-

And as she fucked me deep and swift, her hands grabbed both my wrists and pulled them down to my sides, pulling our sexes as close together as they could be. I was now moaning with abandon, bucking up to meet her rapid strokes, my toes curling and pinching at her reddened nipples. She was moaning now too, her sweet mouth shaped into an 'o', her neck and chest flushing with her own orgasm.

And then it came.

We came.

Together.

14.

I felt her turn to liquid inside of me, and at the same time I felt as though I was melting all around her. Her frankly godly phallus unloaded deep, thrusted deeper to impregnate me. Filling me with more love than I had already been unable to handle.

Something smacked me in the chin then and my eyes opened wide in surprise. She hadn't touched me. She still had hold of my wrists in a vise-like grip and was cumming, cumming, cumming, endlessly it seemed.

It happened again quickly, another smack and then another, and then it rained down on me. I was cumming, to say the least. In fact I was exploding all over myself. Such was the force of my ejaculate, it had hit me hard enough to startle me.

But I hadn't noticed right away because nothing had startled me quite like the immensity of the orgasm ripping through my body. Emotionally I was now devastated. I couldn't feel my arms or legs.

For the first time in my life I was filled with a profound sense of goodness, all of the happy feelings and feelgood hormones, while instead I felt numbness throughout a body that had become in time receptive only to aches and pains.

15.

Around 2am we were high as kites and giggling like kids, naked as the lord intended and cuddling. We'd taken a cool shower and were still damp. The coolness of the morning air was welcome indeed.

I couldn't stop kissing her and the fact that she didn't stop me kept me coming back for more. She asked if this meant I had feelings for her. I told her yes, now that she had opened me up. There was no going back and I didn't want to. I was filled with all kinds of lovely feelings for her, and I wanted to pursue those feelings if she did too.

Sleepily she told me that she really liked me, had feelings for me too. That's all that mattered as we held each other and drifted off to sleep. How the world would react to us from the next day onward, that didn't seem to matter to me at all.

I had come completely unbottled, my soul set free. I'd somehow figure the rest out.

Just as soon as I'd regained the use of my legs.

12
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RandyPanTheGoatBoyRandyPanTheGoatBoy7 months agoAuthor

@ShortyMac it's a sad world we live in, meth is a scourge on humanity. Prime example of how addiction makes people's decisions for them. I hope Summer found her way in life.

ShortyMacShortyMac7 months ago

Damn that was so hot. That story reminded me of a couple of flings I had with a transgendered m2f. One the first was just a sexual encounter Dawes never saw each other again. The last one was a hot black trans girl I met at a homeless shelter in 2017. We became friends and her to female roommates and I played Spades to pass the time. In March 2018 I finally got a one bedroom apartment. Summer and her roommates thru a house warming party before I even had a chair to sit in. They brought food and four folding chairs. Then I got furniture and every Saturday night Summer came over for dinner and a movie. We talked a lot but never had sex. We did talk about sex and she told me honestly that I wasn’t her type. She admitted she was a size queen. I’m not exactly small or huge just a bit bigger than normal at 7 inches. Then all of a sudden in July if 2021 she just disappeared. I tried to find her but couldn’t. Then in November about midnight she showed up at my door. She was homeless again and starving so I fixed her some food. After she was full of food we were sitting on the couch talking and she had the strangest look on her face. She looked at me and said

“You want to touch it?” YES I told her. She untied the belt holding up her sweatpants and pulled them down. My jaw hit the floor. She was already hard and was HUNG. We’re talking 10 inches and as big around as my wrist. I immediately. Started sucking her. I was only able to get half of her in my mouth. I sucked her for around 20 or so minutes. Then I ask her to fuck me. We tried several different positions, but she was just too big for me. I went back to sucking her for another 45 minutes. She never came. I gave her the bed and I slept in my recliner. Next morning when she got out of the shower she walked into the living room and she was hard again. So for another hour I tried to get her to cum. Nothing. That next night I found out why she was hard all the time and didn’t cum. She was smoking Meth! I had to ask her to leave because her smoking Meth in my apartment was grounds for my being evicted. She got real mad and told me if she left I’d never see her again. That hurt telling her to leave as I did have feelings for her. When she came over weekly for dinner and a movie she was so sweet.

RandyPanTheGoatBoyRandyPanTheGoatBoy7 months agoAuthor

@RangeExpander thank you for all of your encouraging compliments.

RangeExpanderRangeExpander7 months ago

Wow, you are amazing! You write so well and your story is SO hot! Thank you.

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