tagTranssexuals & CrossdressersGrannie Panties Ch. 02

Grannie Panties Ch. 02

bygrgy56©

Note: This submission includes cross-dressing and incest. If neither of these topics interest you, DON'T READ IT! I am tired of anonymous bullies who don't have the guts to comment with their handle so we can read how great their submissions are. Therefore I will now start to remove these types of comments from my submissions.

To everyone else, thanks for your patronage and complimentary comments. I hope you continue to enjoy. And now more Grannie Panties...


Chapter 2

I had just discovered some of Grannie's panties and lingerie in her basement laundry room. After I stripped off my clothes and my own baby blue cotton panties, I dressed up in her matching tight corset and panties. I was using a different pair as a cock stroker. I was about to cum when Grannie came to check on me...

"Jeremy, is everything ok.. Oooh!" Grannie suddenly appeared to check on me. "Oh my!"

I couldn't stop and shot my wad as she stood there and watch me. When I finished she said. "When you're done with them... Come upstairs to talk."

As she turned away, I muttered to myself. "Shit!"

"I heard that!" Grannie called back at me. "Little girls don't use curse words."

With a little guilt of being caught but a lot of regret of having to take off her things, I redressed myself in my own panties and clothes before going up to see Grannie. She was sitting in the living room and nodded to me to take a seat beside her on the love seat.

She looked at me. The ticking of the grandmother clock was the only sound. Finally, she broke the silence. "Now Jeremy, how long have you been wearing women's underwear? Does your mother know?"

"For a while now. Yes, she knows. In fact she bought me the panties I have on right now." I confessed. "I'm not gay. I just like wearing women's underthings."

"She bought you underwear?" Grannie asked surprised.

"Yes, Grannie. She bought me a number of things. After she found out that I was stealing her panties to wear and masturbate in, she bought me my own panties, bras, garters and stockings. I wear them as much as I can; sometimes even when I go out." I explained. "And sometimes I still wear hers. She has some really nice pieces."

"Hmm... Did you know your grandfather also liked to wear women's things?" Grannie asked me. "Maybe that's where you got it from."

"Wha..? Grandfather? You mean Gramp... your husband, Billy?" I was flabbergasted. "He wore....?"

"Yep. I use to dress him up and we'd fuck like rabbits. He had his own maid outfit that he used to clean the house in. He had a nice, tight, round ass and great legs for a guy. Looked great in stockings." Grannie explained further. "But I don't think his cock was a big or hard as yours."

"My grandfather was a cross-dresser?" Her words swam in my head. I couldn't believe my ears. "Grannie used to dress him up and made him clean the house? Fuck like bunnies?"

"In fact, I bet you would look incredible in his maid outfit." Grannie smiled. "Would you like to try it on? I still have it. I bet it would fit."

Without waiting for an answer, Grannie took me by the hand and lead me to a back bedroom. One side of the walk-in closet was filled with different women's clothes all preserved and covered in clear dry cleaner's plastic bags. The other side had some shelves stocked with different paraphernalia. "This is your grandfather's closet." Grannie riffled though a couple of items before pulling out an outfit. "Ah, here it is. Put this on."

I took it from her but just stood there unsure of what to do. Grannie found and handed me a new package of stockings to go with. "Go on! Go put them on! I don't want to have to tell you again, Jerem... Alison!"

"Alison?" I shook my head trying to comprehend what was going on. "Did Grannie just call me Alison?"

"Yes, I called you Alison. That was your grandfather's girl name. I thought you would like it too since you're going to wear his girl clothes." Grannie told me. With some trepidation, I stripped off my shirt and bottoms. I hooked my thumb inside my panty waist and paused. Grannie stood there looking at me with her hands akimbo. "Well? Your panties are very nice and pretty, but you won't need those ones."

I pushed down them down to my knees and let them drop to my feet. Grannie's eyes popped when she saw my cock. "Oh my god, Alison. You do have a very beautiful cock. Nice. Clean. Uncut." Grannie dropped to her knees in front of me. She took me in her mouth. "Mmm... Definitely bigger than your grandfather's."

Grannie grabbed handfuls of my ass and pulled me into her face. I felt my cock slide right down her throat. Her nose pressed against my short trimmed landing strip. "I guess Mom got that ability from you, eh Grannie?"

"Cough!" Grannie almost choked on my cock. "You and your Mom?"

Suddenly embarrassed. "Yes, Grannie."

She stood up and gave me a stern look. "Get dressed."

I removed the plastic and the hanger. First I laid everything out. Then I held the waist band open to the frilly pink panties with black accents before stepping into them and pulling them up. They didn't reach my waist but hung around my hips. My bum filled them perfectly. Next was a waist cincher. Grannie helped lace up the back tightly; tightly enough with the bone stays to make it a little difficult to breath. She also helped me on with the black bra. The cups were made with a gauzy nylon material but were way too big for me.

"Wait!" Commanded Grannie. She disappeared back into the closet and reappeared a minute later. She pulled open my empty bra cups and inserted some silicon breast forms with big, hard purple nipples. She adjusted the bra straps and looked at me. "Very impressive. Your grandfather always loved big tits so he got D's."

When I pointed my toes and slid the stockings up my hairless legs, Grannie asked who showed me that. I told her Mom did. Grannie smiled as she made sure the dark seam up of the pink stockings ran straight along the backs of my legs. I clipped them to the dangling straps from the cincher. Then she inspected the rest of me and started to cry. "Oh my goodness! You look just like...."

The dress was next and I had some troubles with them. I raised my arms up so Grannie could pull down the maid uniform down over me and zipped the back. With the corset, the dress fit me perfectly. The front was low enough to show my deep, big cleavage. The white pinny stopped just under my breasts. The fairly short hem barely covered the welts of my stocking tops.

"You look very pretty, Alison." Grannie smiled at me. "Put your shoes on and I'll fix your make-up."

The shoes were black, strappy Mary Janes with a skinny four inch heel. It was the first time I wore women's shoes. Actually it was the first time I ever wore a women's dress or outfit. I never thought of dressing Mom's dresses; not that they would have fit anyways since she was much thinner. Standing and walking in my new shoes was to say an adventure, but Grannie showed me how to balance myself and walk. Soon it was like I was born with them on my feet.

We sat at the dressing table which was covered with make-up. This was going to be the first time that wasn't Halloween that I was going to wear make-up. She did my face and plucked my eye brows. She glued on some long false eye lashes before she applied shadow, liner and mascara. Finally she applied some fiery red lipstick and liner. After I blotted on some tissue, she painted on some gloss to keep it from smearing.

Grannie had me put on a skull cap over my short cropped hair and then place a black wig on my head. It was kind of a short pixie cut which looked really cute on me. "How do you like yourself now, Alison?"

I stood up in front of the full length mirror and was amazed at my transformation. I didn't even look like a boy anymore. Just a cute girl in a maid's outfit. All I could say was "Wow!"

"Mmm... You look so much like your grandfather." When I looked at Grannie, her eyes were as big as dinner plates and her smile was bigger than a crescent moon. "So fuckable looking too!"

Grannie moved behind me and kissed the nape of my neck. Her hands reached under my arms and hugged my body. She ran them up and down; squeezed my fake breast and pinched the nipples. One of her hands sneaked under the hem of my dress and into my panties to stroke my cock. "My god, your cock is hard again? Didn't you just cum?"

"Yes, Grannie. I just seem to be able to get hard again really fast." I confided. "Included downstairs, I've already cum four times today!"

"God, Alison. I want your cock inside me." Grannie told me. "Help me off with my dress!"

Playing the good maid, I unbuttoned the front of Grannie's dress. Save for her panties, she was naked underneath, but her body was incredible; tight, smooth, curvy, beautiful. Like Mom, her ass was perfect and her legs were long and shapely.

I knelt at Grannie's feet. I looked up into her wild eyes. She gave me a slight nod. I pulled aside the soaked crotch piece of her panties. Her cleanly shaved cunt dripped with wet. I used the tip of my tongue to tentatively lick the juices from her slit. She moaned. I took it as a signal and increased my efforts until my tongue was as deep as I could penetrate her. She came on my face.

"Oh god, Alison! It's been so long since I've felt that!" Grannie cried out. "Only girls can make girls feel like that!"

I made her cum twice more before she had to push me away. "Stop! Enough! Fuck, I can't take any more. I want to feel your cock inside me!"

Grannie laid back on the bed as I moved between her legs. Her cunt looked like it was made to be fucked. I pulled down my panties slightly and pushed my rock hard bone into her. "My god! She was just like Mom! Hot! Tight!"

"Oh yes, Alison! That's it! Fuck me!" Grannie dug her heels into my ass. "Oh yeah! Cum inside me, Alison! Cum in me now!"

I felt her squeeze her walls; her cunt seemed to be sucking my sperm from my balls. I shot my hot, white, sticky load into my Grannie!

"Oh fuck yeah! Oh fuck! Oh fuck! Oooo...!"

I collapsed on top of her.

It took a little bit before Grannie caught her breath enough to speak. "Oh, Alison! That felt so wonderful! I haven't cum that hard since.... I can't remember."

I slowly pulled out from her. She spasmed slightly as I did so. She asked me rhetorically. "Is this how your mother feels like after you fuck her? God! No wonder she keeps you to herself."

We cleaned up a bit. Grannie showed me how to fix up my make-up on my own. My panties were a mess; so I ended up changing my outfit. Grannie had me put on a school girl's tunic which included a very tight, white bra with the breast form, white cotton thongs, white thigh highs stay-ups, a white silk blouse that was half unbuttoned and short red plaid kilt. I still wore the Mary Janes I had on earlier.

I'm not entirely sure why but as I moved and walked about, my stocking kept slipping down. Grannie gave me a white garter belt to hold them up. The short skirt did nothing to hide the straps.

Grannie had me change my hair too. I took off the short black hair and replaced it with a fiery red wig. The flowing locks fell over my shoulders and partly covered my breasts. "My god! I look like Raj's girlfriend Emily from Big Bang!"

"You look... I want to fuck you again, but my poor pussy is still a little sore. It isn't use to such a big thing inside it. You are definitely bigger than your Grandfather's." Smiled Grannie.

Grannie went to change so I went downstairs and made some tea. I got some of her famous butter cookies on to a plate. When she returned, we sat in the living room and talked.

"... and that's how I got started wearing Mom's panties."

"And she found out so now both of you fuck?" Grannie asked.

"Yes. Like I said, she caught me playing with myself on her bed dressed in her things." I chuckled.

"What?" Grannie looked at me quizzically.

"Mom caught me again this morning." I couldn't help but chuckle some more. "I came all over bra and panties so she couldn't wear them to work. Apparently, she wanted to wear it under her business suit and use it to persuade (air quotes) her boss for a promotion."

I'm not sure if she understood the reference but Grannie continued her questioning. "Have you ever gone out dressed up as a girl?"

"No. I only wear my girl things under my boy things." I confessed. I could feel myself get hard.

"Yeah, I can tell you've never dressed up and went out as a girl." Grannie mocked. "Little girls don't sit like that and show their treasure!"

I didn't understand. Grannie looked and nodded towards my legs. The short skirt had ridden up high enough to expose my panties. My cock had slipped through a leg hole in my panties and was apparently visible to Grannie since my thighs were parted.

"Little girls need to learn to keep their knees together and sit like a little girl." Grannie scolded me. "But I guess you aren't a proper little girl. Dressed like that and sitting like a slut, you deserve to be treated as one."

Grannie stood up and moved towards me. As she did, she lifted her skirt up slowly. She was wearing opaque black stockings. As her hem exposed her garter clips, something between her legs started to appear. A black strap-on cock; about six inches long and not too think around. She wasn't wearing any panties.

By the time Grannie was standing in front of me, her skirt was around her waist. She held the back of my head and forced her cock into my mouth. She used back and forth rocking motions to feed it deeper and deeper into my mouth. I felt it hit the back of my throat. Surprised, I coughed slightly and wet goo came out of my nose but I didn't feel like gagging. Soon, I relaxed and was able to accept it all.

Grannie was standing between my wide spread legs and freely pumped my throat. As she did, I could feel her stocking legs rub against my exposed hard cock.

"Oh Alison you dirty slut. You know what I like, don't you? That's it suck my cock. Get it nice and hard and wet and ready!"

I was too entrenched in my task and failed to comprehend but I doubled my cock sucking efforts.

Grannie pushed me away and shoved me onto my back. She lifted both my legs up and ripped my panties to my thighs. Then I realized and started to protest but too late. Grannie used my own saliva on her cock to lube my asshole. When she thought it sufficiently wet, she slowly pushed it in.

"Uuuuhhh!" I screamed. Never having anything pushed in, I was in agony and ecstasy but mostly the latter. Grannie was kind and took her time to let me get used to it. But once I started rocking my ass back and forth, she fucked my virgin ass a little more aggressively. I spread my cheeks wider hoping she could push more of it inside me but it was all the way in. Grannie grabbed hold of my boner and stroked it. The feeling was intense and I was about to shoot.

The front door opened. "It's me! I hope you don't mine me using my own key. Is Jeremy still here..."

I managed to turn my head to see Mom standing there. Grannie gave me one final hump and I started shooting my white sticky goo. Grannie aimed it up. It splashed my face and red hair. My red painted lips were agape in an orgasmic "O" as cum landed on my tongue. As I looked at Mom, strings of cum dripped from my long false eyelashes.

Mom's mouth was open with astonishment. The only thing that came from her mouth was a surprised "Oh."

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by Anonymous

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by chimpee01/26/17

WET WET WET

Need to change like Allison and Grannie I've just cum

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by sissysimmi12/29/16

wonderful

Omg tho divine Alison is such a lucky gurl. I wet my thong just imagining being her. Alison might help her mum get the promotion giggle. Keep going its hot.

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by MarcelLove12/25/16

This is one of mine....

Greatest crossdressing fantasies, but just the other way,
first my mom fucking me with a strapon
and then later mommy and grandma together,
Fuck me with two Strapon's.

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by JanetHarper12/23/16

My goodness

Your story left me with a wet spot in my panties.
What a family! Alison certainly is a lucky girl. Looking forward to what her mom will say (or do). Maybe you could write about her moms exploits at work.

PS:more...

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by MonicaCD12/23/16

Great story so far

Love it so far. I just wish the chapters were a bit longer. I look forward to more from this open minded and fun family

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