tagTransgender & CrossdressersHouse Calls Ch. 01

House Calls Ch. 01


For a while I had an apartment in the city, it was a good time. It was when I learnt the ins and outs of life, and discovered new desires and different ways to fulfill them.

It's when I went from being straight to bi, and then to a strong preference for gurls. I'm quite happy about my journey, but when I tell someone about this there's this default assumption that I'm only talking about the "young cross-dressing femboy twink" types. So I feel the need to speak up about all the other "types" I've been with.

I've been blessed to always have some partner available to drain my balls, and part of the secret is a wide diversity in my partners. Yes, there are tons of the younger kind, but a few in the middle, and then several of the older kind too.

Having an older (actually, much older) lover can be really good. Unexpectedly good. Life is full of tradeoffs, and there are different people for different occasions, but older sissies have a lot to offer, and they have really enriched my life, so here's a story about one of them.

Larry had retired early and had an apartment of his own on the other side of town. Later I'll talk more about how I met him for the first time in a Starbucks, both of us a little nervous, or the second time, when I invited him home but he was still nervous and we watched porn together, but right now I'll take us back to a day about a year into our "occasional meet up relationship".

He lives in a high-rise apartment building, in the middle of a row. I knock once and the door opens immediately. Larry is a hugger, and pulls me in. He's wearing a Hawaiian shirt and shorts. The door closes, and he jumps my face, kissing me wildly.

He's 51, divorced, and was of the generally lonely, miserable type when I found him, but is perky and happy now. He takes care of his health, goes for walks, and makes sure to tell me every time we meet I bring some meaning to his life.

I'm running my hands under his shirt. He's a bit chubby, but has smooth skin everywhere. "Mmmm," I break off the kiss, "how've you been?"

"Oh the usual, went for a walk with the guys, hung out at McDonalds. Was gonna go for my haircut today, but ..." he stroked my chin, "I've decided to grow them."

I lean in closer, "for me?"

"For you."

I nibble his neck and he moans. "Oh and last week I watched all of the videos you sent. Got me hot. Got me real hot for you."

Larry is not very online-savvy, and after I showed him what you can watch for free today, and gave him some pointers, he just can't get enough.

"Okay," I say when we were inside, "when we're indoors, we take our clothes off."

Larry does a double take, but I stare firmly at him, then walk up to him and kissed him on the lips. "you know it's just to break down the barriers between us," I kiss him again, "darling?" I unbutton his shirt and stroked his skin, leaning in to whisper in to his ear.

It's all about the mental effect, something I learned a long, long time back. We have sex with our bodies, but within our minds.

"My sweet, sweet darling, I love your skin." I kiss his neck, hearing his breathing quicken. I undid the buttons of his shorts, dropping them to his feet and letting him step out of them, leaving him in his panties.

Being a bit on the plus side, he liked large silky ones. He cared more about the feel of the material than the look, so they were mostly all quite plain, though this one had a small frill running along the top, with a tiny bow in the front.

I stood back to admire, then cupped him through the silken fabric, making it rustle. He wasn't hard, but the material was soaked with precum. I squeezed softly, and nibbled on a nipple, making him moan.

"You look good, baby," squeezing both nipples lightly, before moving my hands towards his neck, massaging and ever-so-lightly choking, "now it's daddy's turn."

It was a kink we had discovered a long time back. If I remember correctly, the very first time we met, over coffee, he had been hesitant and withdrawn, we were talking back and forth, until I said in an exasperated whisper, "but don't you want to just relax and be yourself?"

And seeing his face soften, added: "don't you want to be yourself for ... for daddy?" I placed my hand on the table and waited for him to do the same, and closed my eyes. In a moment, his palm was within mine, I had opened my eyes, and we were smiling at each other, smiling with a new connection, a new understanding, a new shared desire for the future.

The initial awkwardness (given our ages) was over in the first two meetings, and though this isn't something I do all the time, never insisting on it with my younger lovers, Larry really took to it with gusto, seeming to find in these roles the fulfillment of some deep desire.

And so it was today. "Yes daddy, let me help you out of these clothes." We played with our tongues as he unbuttoned me. Peeling off my shirt, he rubbed my chest. I raised my arms up, and he nuzzled his face into my armpits, "oh yeah, papa bear, oh yeah."

I laughed and hugged him, "slow down, honey, we've got all day!" He undid my trousers and slid them down, helping my feet out one at a time, then folded them neatly and kept them to a side, before kneeling in front of me, resting his face against my briefs.

"I love your smell, daddy, all over you. Your face, your arms, your chest, your legs, your dick." I didn't want to cum so soon, but Larry was making me hard. "Let me take care of you, daddy, let your little baby cub relax you. Can I?"

"Fuck," I sighed, looked down, and nodded, giving permission. He gleefully pulled my briefs down, and just engulfed my cock.

Larry had no gag reflex at all. In some sense he knew that his mouth was really all he had to offer on most days, and had really put in the work to be able to totally relax his throat.

I lurched inside his mouth, with the shock of suddenly being surrounded by a warm, welcoming orifice. I pulled out and held my cock up. "You'll get this later, suck my balls, show em some love first."

Larry licked them lovingly, holding each one and licking all around the sac, hitting them with the tip of his tongue, then gobbled them up, bathing them in saliva. "It's ok, daddy, you can talk dirty to me for a bit, you know I like it."

"Alright, baby bear, there's no going back now. I'm going to fuck you." I put two fingers down his throat, wiggled them around. "This pussy belongs to me. It's mine."

Larry opened wide and stuck his tongue out, "yeah daddy, it's your pussy, fuck it. Use it."

We got into a familiar position, as I crouched over him and cradled his skull and neck, and he let himself open upwards, holding onto my thighs. I went in balls deep, and rested there.

I stroked in and out, slowly, deeply, savoring the sliding, the tightening. "Whoops, almost forgot. Stay right there baby."

I grabbed a towel, folded in twice and laid it under us, then got back into position. In and out, getting sloppier and sloppier, I was on a slow burn and wasn't to keep going as long as I could.

Drool dripped down steadily, as I breathed deeply and sawed in and out, throat and mouth turning into this moist, hot, wet cauldron for me. The world receded, and was replaced by my sighs and the sounds of slurping and gagging.

"Oh yeah, feels so good honey, so hot and tight, yeah lick my balls, just like that. Going to feed you soon, going to feed you my cum." Larry just nodded imperceptibly, and brought a hand up to stroke my balls.

That did it for me, and I grabbed on to his head, as I roared and emptied myself.

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byIcelandSpar© 1 comments/ 5782 views/ 2 favorites

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