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Oldie Goldie Ch. 01

Story Info
An old, mature crossdresser came into my life ...
1.1k words
4.28
19k
5

Part 1 of the 2 part series

Updated 06/08/2023
Created 05/06/2017
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His smiling old face greeted me at the table.

"Hi," I said as I sat down.

We had arranged to meet for coffee near my place. He had messaged me saying he was a friend of Albert, one of my old lovers, and would I be interested in getting to know him?

"Sure," I had replied back, and here we were, getting to know one another. Steve was married, had two kids, then divorced. So similar to me, just a decade and a half ahead.

It was warm and sunny outside, and I sipped my iced coffee as we talked, noting his glasses, wrinkles, large checked shirt, and earrings.

"Look, I'll cut to the chase," he said at last.

"Please do."

He sat up, rotated his chair around our little round table, and sat down again. "I'm lonely, and Albert said you might be interested."

He slipped his foot out of his sandals, and rubbed it along my leg. I took my foot out too, and he placed his above mine, his toes curling in.

"I would be. I mean, I am, yes, It's just that you're ..."

"Old?"

"Well ..."

It seemed like a shadow passed over him for a bit. "Albert said that for you, this wouldn't be a problem, he said ..."

"Hey, hey, Steve, relax, I was just about to say that I'm not so much into one night stands any more. I need someone to be around for a few months."

He nodded, "well, I'm retired now. I got time."

He brought his hand over to my crotch, and confirmed to both us my growing bulge there. I reflexively looked around, but of course no one cared enough to look at us.

"Look, Steve, can you even ... I mean ..."

"Bottom for you? Offer you my ass pussy? Not for a while, I'm sorry. Don't ask. Maybe in a couple of months."

Then, seeing me start to shake my head, "I can understand if you want to wait, or even say no. But if you trust me, we can be happy together."

The crowd murmured around us as I stared into my cup, his fingers lightly scratching me, his face looking at me questioningly. Resolved, I stood up, and patted him. "Let's go."

Clouds had drifted into the sky as we exited, and a wind had started to blow. We waited at a stop sign and smiled at each other.

"It's just a first for me you know," I felt I had to explain. There's a lot I don't know. I'll have a few silly questions."

"It's okay. It's gonna be good." He brought his hand next to mine, and interlaced our fingers.

"Tell me," I leaned in a bit, "do you still get hard?"

"Not for the last five years," he chuckled, "but I can still cum. I did today. Just before we met."

He brought the fingers of his other hand to my nostrils, and I sniffed deeply, sniffing in the familiar, raw smell."

The light turned green, and we walked on.

I unlocked the door to the building, and he entered. We walked to the door of my apartment, and as the doors closed, kissed each other hard.

"Let me see you," I said, unbutton his shirt and sliding his shorts down. He wore nothing underneath. I put a hand on his lightly furred chest, and cupped his shrunken genitals with the other, finding myself able to enclose them entirely.

"Yessss," he hissed out, throwing his head back.

I massaged them, and he collapsed on my chest, moaning. I guided us to a sofa, and sat down. As I stroked him lightly, with a thumb and finger, he kissed me wildly, almost desperately. He stiffened a little bit but remained mostly flaccid, until a point where he gripped my neck tightly, and spasmed, and loosed three little spurts into the palm of my hand.

"Thank you," he sighed, and slumped backwards, as I continued to sit where I was, with my hand out.

"So happy that's out of the way. Look, let me level with you. I'm old enough to have pretty much been there, done that, I just want to spend the rest of my days happily. And what makes me super-happy is to be someone's sex slave."

Seeing my initial shock, "but I don't mean in the hardcore way, necessarily. I mean, okay, I'm into that, but it's cool if you're not." He grinned, "actually, it's probably better. Don't think I could take a lot of physical stuff."

Holding my hand with his hands, he brought it to his mouth, and pressed it down, then rubbed it around. I took the cue, and smeared his lips with it.

"I fucking love cock, but I'm tired of jumping around beds, and taking the usual risks. So if you don't have any attachments right now, or for a while, I'd like to hang out with you, and just, you know, be there for you in every way."

"I ... well, I do have space, and I could use some help around the place, and I am too busy to date steadily at the moment, so .."

"So it's a deal, sonny. Come on, open up, let momma take care of you. Now that you've emptied me, I can really be your bitch."

He wiped his face and seemed to consider something for a moment. "Ah, this is unusual, I've left all my makeup at home. Well, the first time will just have to be this way. You okay with that?"

I shrugged off my shorts and underwear, and sat back. "Not enough space, let's go to your bedroom. Or, okay, we can make this work." He brought a pillow and sat down, then inhaled my dick.

He looked up at me, and I was suddenly overcome with this sensation deep inside me, and almost involuntarily, I came immediately, shuddering, emptying into his mouth.

He swallowed the first two spurts, then closed his eyes and pulled me out, placing me on his forehead, where I continued three or four additional spurts, that covered his eyes and trickled down the side of his nose.

"Stay," he mumbled into my balls, and held on to my legs, as I slowly deflated, the tip of my cock contracting until it ended up at his nostrils. He inhaled deeply a couple of times.

"Yeah, I love your cock. Look, this is who I am, this is what I like. Tell you what, I have my stuff packed already, I'll bring it over tomorrow morning and settle in. Sounds good?"

I stared at his cum-glazed face, and nodded meekly.

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4 Comments
gazzclubgazzclubover 3 years ago
Different is good

Really enjoyed this for its realistic details and down to earth qualities.

MarieJoanneMarieJoannealmost 7 years ago
So true

Sigh , yes bowler. Too true. Oh for the knowledge we had in youth !!! And the courage to be true to ourselves !!! Marie

IcelandSparIcelandSparalmost 7 years agoAuthor

I feel the same way, and am encouraged that someone else feels the same way. Love, my friend, from my heart to yours!

300bowler300300bowler300almost 7 years ago
LOVE IT

I LOVE SEEING STORIES OF OLDER LOVERS, YES WE ALL CRAVE THE STORIES OF THE YOUNG AND DREAM OF BEING THEM, AND BEING TREATED AND USED IN THAT WAY...BUT, LETS ALL BE HONEST WITH EACH OTHER, AND THAT IS MOST OF US WHO READ THE STORIES ABOUT CROSS-DRESSERS, ARE OLDER AND IN THE CLOSET, AND DREAMING OF FINDING A LOVER OF OUR AGE, TO DRESS AND PLAY WITH, THEN GO BACK TO OUR CLOSETS, TILL WE CAN GET AWAY AGAIN...

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