The Sissy that Grandma Loves & Grandpa Hates

Little girl party dress on the outside, whore lingerie underneath. Carl gave a sultry look over his shoulder, then shook the long, curly brown hair out of his eyes and strutted around the bedroom like a wanton little wench while his grandma stared at him and repeatedly pinched her inflamed, thumb-size nipples. She edged the tip of her vibrator over her big pink panties toward her clitoris, closer and closer, she held it there and then backed it away, brought it closer again, tickled her clit, but then backed it away again all the while staring at her sissy little grandson lewdly prancing around like an outrageous fag.

With anxious fingers, he reached down and pulled up his Alice-in-Wonderland starched white pinafore then the pale blue party dress and a fussy big ball of cancan petticoats. He pouted his lips and did a bump and grind. With his billowing skirt and slips pulled up out of the way, he massaged his silk panty-covered cock, taunted the old woman and wiggled his slim hips. With a sex hungry stare, she reacted to his every movement, teased herself over and over again, moving the buzzing plastic dildo closer to her clit, then backing it off, moving it closer, backing it off. She was on the floor sitting Indian-style on a big tapestry-covered pillow, naked except for her deluxe full-cut panties. Her heavily scarred pendulous breasts ached, the eye-popping elongated nipples covered with old and new bruises and scratches, but she couldn't stop tormenting them, she never could. They often bled from all the self-inflicted torture, but the pleasure was always worth it. She had learned to love the intense combination of pain and pleasure when she was nursing her first child. Her son, Carl's father, nursed at her breast until he was eleven years old, and from the time he got his first baby teeth, he was a biter. He'd suckle her and bite her nipples. She'd chide him and tell him to be gentle, but the little guy would just giggle and bite her again and again. He knew she liked it. She loved suckling him and no amount of pain was worth giving up that pleasure. It was so pleasurable that she couldn't stop herself from tickling her clit while she suckled him. It was better sex than her uncaring old man ever gave her. A lot of times her son was finished nursing but she wasn't finished cumming, so she encouraged him to suckle some more and pleaded with him to bite her big nipples. He'd bite, she'd cry, he'd laugh, and she'd orgasm one more time. A lot of times their little session ended with her nipples raw, inflamed and bloodied. Even now she often got Carl to pretend he was her little boy sucking at and abusing her drooping tits.

Carl was now standing directly in front of her with his vintage party dress held high, rubbing his pink pantied erection in her face. They hadn't made a merry widow like the one he was wearing in decades; the gaudy red corset had fat black ribbon garters that looked so great to her. She moved the dildo in closer…ah-ah-ah-AH-H-H-H-H! She pumped her hips, shook with pleasure, shouted out and then spilled her cookies. Was this the fifth or sixth time today – she had lost count! But this was the big one. She was expert at timing her last big orgasm to his gushing jism and she knew when he was going over the edge. With her pussy still throbbing wildly and her head buried under his festooning full slips, she gnawed away at his thrusting cock through his old-fashioned pink silk panties, real silk panties. He was jacking himself to climax, and between heavy gasps she fought with his jacking hand to suck up his cum spurting through the wickedly naughty silk and frills. Genuine silk panties and hot and flavorful cum. He was just fourteen but his balls were already big and fully developed. They had been playing sex games for a long, long time.

Carl's legs always gave way as he shuttered through an orgasm. He sank to the floor on top of his pantied granny. Her mouth followed his spurting pantied cock on the way down. They ended up sprawled out on the floor, depleted, in a tight embrace with his cum-saturated panty cock pressed into her face. There was no sound except the continued buzzing of the big black plastic penis, which she had taken away from her clit but now was leisurely stroking over her plump silk-pantied belly, teasing herself with just light little stokes of the fake dong as she and her grandson descended from their pulsating ecstasy. After a few restful, deep breaths, in unison they looked over at the clock on the bed stand. It was five thirty. Time was up. Grandpa always spent Saturday afternoons down at the local gin mill with his beer-drinking buddies. He would be home soon, and he always demanded to have his dinner at six o'clock sharp. Carl and his grandma used every bit of the little energy they had left to extricate themselves from one another, and with an increasing awareness that time was running out, they struggled to clean up and make themselves presentable.

For one so young, Carl never had any feelings of guilt after cumming. Some crossdressers feel so depressed and ashamed after shooting their wad, a guilt trip that robs them of the wonderful afterglow of a great lingerie masturbation session. But Carl probably had no such woes because, from the beginning of his crossdresing, his grandmother provided him with acceptance, understanding, and encouragement. He loved the after-sex sissyboy glow and wallowed in it. He hated it when he had to hurry up after cumming, get dressed and try to appear normal. Fuck normal!

With a whimper, grandma pulled herself up. Her arthritic knees were getting worse, and she knew she shouldn't be down on the floor for these sex sessions. She was getting too old. She told herself she should be finding another position, but sitting there with Carl standing over her shoving his pantied cock into her face was one of her favorite things to do in the whole world. She thought for a moment and then shrugged off the idea: so what was a little pain for so much pleasure.
Besides she was well acclimated to taking her pleasure with a high degree of pain. No, scratch the idea of finding a new position -- bring on the pain!

She sat down at her vanity table and repaired her makeup. Carl remained stretched out on the floor, luxuriating in the moment.

"Carl, honey, some day I'm gonna be gone, and all this will be yours," she said as she took a deep breath and gestured toward her huge, overflowing closet.

It was thrilling to think that some day her dreamy wardrobe of sexy, vintage fashions would be all his! But he couldn't bear the thought of his grandma dying and not being around, and from her labored breathing, he knew she probably wasn't well. Without her, it wouldn't be the same, and that made him sad.

She got up and waddled toward the kitchen to fix dinner. Carl knew it was time to put the things away, but he needed just a little more time. Grandma had given him one of her best pairs of high heels to wear that day. He loved how they looked and felt. Light blue suede with rhinestone buckles that glittered over the open toes. He got caught up in the moment and continued to strut back and forth before the mirror. He could walk better in those steep heels than most of the girls in his class. Better than Betty Jane Dartmun. And she was the fucking Homecoming Queen. He laughed to himself as he remembered how he had to repress an urge to haul her into the ladies room the night of the Homecoming Dance and give her a few pointers on how to walk in them. She had been wobbling something awful.

In the afterglow of sex, it was fun remembering such incidents, and especially for someone so young, he had a lot of girlish memories since he had been dressing up for many years. Done up fancy and fine and frilly. That's how he was now and how he always was in his mind's eye even when he had to do the boy thing. At that dance, under his tuxedo, he was bound up in one of granny's old-fashioned Merry Widows. The bra cups had been removed for the occasion, but he did have the garters attached to stockings – real silk stockings – and the panties he wore were the flimsy, lace-encrusted panties from his grandmother's wedding day! Since they were so old, the elastic was shot, but granny had sewed them up like new with fresh elastic. Boy, that was an exciting night!

But Granny was also proud of Carl as a boy. At school, he was good at track, and she was his biggest supporter. What a great grandmother. She'd go to his meets, root for him in the 1500-meter and then bring him home and play dress up with him. Grandma Moore had beamed with pride when she found out her son's boy was taking Mary Lou Happ to the Homecoming Dance. She was a fine girl from one of Lawton's best families. Her boy was no queer or pansy. She was sure of that. He just liked to play dress-up once in a while. And she could understand that. She loved fancy clothes and had been playing dress up her entire life!