Chestnut (Transgender -- Shemale)

By subslutseven

Published on Nov 30, 2023

Transgender

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The moving company truck was just pulling into the apartment building's parking lot when I left for work, and I spent all day wondering who my new neighbor was going to be. Another broke, fresh-out-of-college dude like me? A family? A drummer with insomnia?

It was just starting to get dark when I got back home. The truck was gone, but a large SUV was in the assigned parking space. As I walked past, I noticed a box sitting on the ground behind the vehicle. I picked it up and knocked on my neighbor's door.

The door opened, revealing an older woman. She was about 5'7", with white hair cut in a long bob, blue eyes, and sharp cheekbones framing a narrow nose and wide, full mouth. She'd evidently been slender when she was younger, and while she'd gotten a little thicker over the years, she was still a far cry from fat. She had great hips, a juicy ass, and big tits. I guesstimated her age at about 65 or so.

"Oh!" she said. "I wondered where that was. Please come in." She stood aside and I carried the box in.

"Just set that on the table, please," she said. "Thank you retrieving it. Are you my new neighbor?"

"Yes, ma'am. Aaron Badem."

"Elizabeth Garland," she said. "But call me Granny Liz. Everyone does."

"Nice to meet you, Granny Liz. Welcome to the neighborhood."

"That's an unusual name, Badem. Where is your family from?"

"My grandfather is from Turkey. It means 'almond.' "

"Interesting. I've never run across that one before."

"The only other ones I know of are all family. Is there anything else I can help with while I'm here?" I asked. I spent some time helping her move furniture and boxes, then got ready to leave. I waved off her offer to pay me. "We're neighbors. I was happy to help."

"Then how about dinner sometime soon?"

"Sure. That sounds great. See you later!"

===

A few weeks later, I was folding the clothes I'd just brought from the laundry room at the other end of the building when I discovered an extra tee shirt in the basket, one I'd seen Granny Liz wear several times. I must have snagged the dryer right after her, though we hadn't passed in the hall. I pulled some sweats over my boxers, grabbed the shirt, and went over to knock on her door. When she answered, I stuck my hand out to give her the shirt, and had just started explaining how I'd come to have it when a pair of sexy black panties fell out of it and hit the floor.

Granny Liz bent to retrieve them and her collar gaped open, giving me a perfect view of what appeared to be the matching bra. My sudden boner didn't quite hit her in the eye, but there was no way she missed it.

She looked at me with a knowing smile. "I'm flattered," she said, "but what would Grandfather Almond think of you drooling over a woman his age?"

"He'd probably encourage me," I said. "He knows I'm more of a chestnut."

Jesus. Had I really just used that stupid pick-up line on this woman?

Granny Liz laughed loudly, and pulled me in for a huge, deep kiss. She kicked the door closed behind me.

Note to self: Use the stupid pick-up line more often.

===

We came through her bedroom door, locked in a heated kiss. She pulled my shirt over my head and pushed me back onto her bed.

"Stretch your arms up behind your head," she commanded. She bound my wrists together and then secured the rope to the headboard. She straddled me, giving me more kisses as she ground down on my hard-on. She started kissing down my neck, then scooted down some so she could nip at my hard nipples. One of her hands was squeezing my cock, the other working at her shirt buttons.

The last button came undone and she pulled off the shirt. She arched her back, making her big tits swell inside the satiny black bra. I could see the outline of her thick nipples through the material. She pulled my sweats and boxers off, and my cock thumped against my abdomen.

Granny Liz leaned over and squashed her tits around my boner. The feel of the cool satin against my hot cock made me even harder. And when she snugged my dick in her deep cleavage inside the bra, I almost came right then and there. She moved up and down the shaft, pausing every once in a while to stick out her tongue and lap up the pre-cum that was leaking out in a solid stream.

She sat back up and reached behind her back. That sexy bra came off and her tits were revealed in all of their heavy, pale glory. She leaned forward, holding them to my hungry mouth, and I sucked and tongued every inch I could reach.

She let me feast on her tits for a little while longer, then slid down my body again to take my cock in her hand. She ran her tongue up and down the shaft and around the head, bathing me in her spit. She put her mouth around the very tip and paused to catch my eyes.

Then she swallowed the whole thing in one plunge.

She stayed there for a moment, letting me enjoy the heat of her mouth and the action of her tongue, then started to slide up and down. Slow at first, but gaining speed. She apparently enjoyed giving sloppy blowjobs, and my cock glistened in the light of the bedside table, while the sounds of her slurping and swallowing echoed.

I tried to hold back because I really wanted to fuck this woman, but she was too skilled and I was too worked up. My hips came up and my breathing stuttered, and I grunted as I filled her mouth with cum.

She let it run out of her mouth to coat my dick, then slurped it all back up and swallowed. She stretched forward to kiss me and gave me a naughty grin.

"I'd forgotten how much cum a young man could deliver," she said, licking her lips.

"I really wanted to be fucking you for that," I said.

"Oh there's lots we can do while you recover," she said. She patted my cheek and got off of the bed. She unbuttoned her jeans and turned her back to me. She hooked her fingers into her waistband and pushed the denim down her legs, bending over to give me an eyeful of her ass wrapped in another pair of black satin panties, with lace trim framing her waist and thighs. She slowly lowered the panties to the floor, revealing the flawless pale expanse of her plump ass cheeks.

"Oh fuck, Granny Liz," I said. "I gotta have that ass."

"You will," she said. "But first, you're going to..." She turned around and waved a 7-inch prick in my face. "Suck Granny's dick!"

She climbed onto the bed, her knees to either side of my head, and pushed that hard cock deep into my mouth. Her hips rocked back and forth as she fucked my face, and I couldn't do anything but take it. I tasted her salty pre-cum on the back of my tongue.

"Ooooh yeah," she cooed. "I like that." She pulled out of my mouth and slapped my face with her dick. "Lick it, boy," she ordered.

I ran my tongue all up and down that slippery meat, wanting to please Granny.

I was getting hard again, so she repositioned herself head-to-toe, and we got into some serious 69 action, each of us trying to outdo the other. I lost by a mile. Granny Liz had more than 40 years on me, and knew tricks I'd never seen. She could have made me come again, but she stopped before I slipped over the edge. She turned around and squatted over my dick, grabbing it at the base and slowly sliding down onto it. She paused for a moment, then started pistoning up and down, fucking her ass with my tool. I could feel her tight asshole gripping me whenever she was seated to the root, and I held out as long as I could.

My second load was nowhere near the size of the first, but the electricity doubled, and shook as I tried to get even further inside her. She rocked her hips in time, milking every last drop.

Granny Liz climbed off of me. "Flip over," she said, and I did. She had me raise up so she could slide a pillow under my stomach, and then she rummaged in a drawer. The mattress dipped as she got back on the bed and knelt behind me. I felt warm oil dripping down between my cheeks, and she used a finger to lube up my asshole.

When she judged I was prepped, she set the lube bottle aside and nudged in closer. She used one hand to pull one cheek to the side. The other hand lined up her cock, and she slowly inserted the tip. Once she was set, she took hold of my hips and pulled. She gently worked her shaft in and out until she was finally able to sheathe it all the way inside my ass, and I felt completely full.

She started slow, but got faster as I relaxed, until she was slamming her hips against me. I felt her balls smacking into my ass as she panted with the effort. Despite the two huge orgasms I'd already had, damn if my cock wasn't getting hard again. Granny Liz must have had some sixth sense, because as soon as I'd noticed my hard-on, she reached around with one hand to grab it and stark jerking me off in time with her fucking.

I was panting faster with yet another growing orgasm, and we finished at the same time. I was shooting blanks, but I felt a hot river of Granny Liz's cum flood my asshole. She squelched back and forth a little while longer, until her softening dick slipped out on its own. She untied my hands and laid down beside me, giving me a long kiss and rubbing my arm. Her warm tits pressed against my chest.

"So what are you going to do with all of that extra money?" she asked.

"What extra money?"

"The money you save on rent. I'm moving you in here to be my permanent fuck puppet."

Hello, lovely readers! It's your friendly neighborhood bi subslut, Savannah. I hope you enjoyed the story. Want to be the star of the next one? Just send me a hot pic and you could be! Hard cocks, boobs, I love it all. And gurls, let's see your sexiest lingerie. Bonus points if you forget to put on your panties! I'll post a personalized story for the winner at the beginning of each month. Ta!

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