Grannie Panties Ch. 03

I found out that my maternal grandfather, Grannie's husband was a cross dresser with a whole wardrobe of women's clothing. I modelled his maid's outfit which brought back a flood of memories for Grannie. Later, she had me change into kind of a school girl's outfit. Then my mom just walked in on Grannie fucking my virgin ass with a strap-on and me cumming all over myself.

Grannie slowly kept pumping my ass with her silicon cock as dribbles of cum still dripped from me. Between the long eyelashes and the strings of cum on my face, it was difficult to watch Mom but her reactions was really funny.

Grannie gave me one more big hump then realized someone was watching. She gave me a wink and turned to Mom. "Oh hi, dearie! Sorry you caught us in a little er..r moment. This is Alison. Alison, this is my daughter, Lora."

Grannie finally extracted her cock from my asshole. I fixed my panties and brushed down my skirt. Mom looked at me strangely. I thought she might recognize me immediately but I guess with the make-up and sperm all over my face, it was a bit difficult. Also since Mom had only bought me slightly padded bras, the huge D sized breast forms really changed my look. I extended my hand. "Hello Lora."

"Uh... Hello Alison." Mom took my gooey hand. She opened her mouth to say something, but nothing came out.

"Oh, Alison is my new girlfriend. You know since your father passed away, I've been pretty lonely." Grannie smiled. "Isn't she pretty?"

"Y..e...a..h..." Mom said uncertainly. She still eyed me suspiciously. "I... Have we met...?"

I couldn't stand it anymore. I didn't want to stop the tease and reveal Grannie's and my secret, but. "So how did your meeting with Mr. Cummings go today? Did you get that promotion? Did he like your sexy bra and panties?"

"Yeah, fine... Wait! How do you know about the promotion and what I wore?" Mom glared at me. "The only other person who knew was... Jeremy? Jeremy, is that you?"

Grannie and I laughed at the revelation that Mom just figured out. She just stood there staring at me. Her eyes were like huge moons and were scanning me up and down. "What do you think? Like my new look?"

"Oh my goodness, Jeremy! I didn't even recognize you at all!" Mom finally was able to babble. "And who is Alison?"

I opened some wine and we sat down in the living room. My face was still caked with my dried cum but at least I could now see where I was going. Grannie and I explained the events of the day. "But we really didn't think you would find out this way. I hope you're okay with this."

"Yeah, I'm okay. I just can't believe how pretty you are." Mom kept repeating. "I love your big breasts."

I needed to break the cycle. "So did you get the promotion?"

Mom didn't say a word. Instead she stood and slowly pulled up her skirt. Her stockings were stretched and laddered with obvious signs of dried cum on them. She no longer was wearing her panties. Her pussy was wet, red and swollen. "Does this answer your question?"

I ran up and gave Mom a hard hug. "Oh congratulations! Tell us what happened."

"Well after you filled me with your load this morning, I made it to the office. Mr. Cummings called me in and I locked the door to his office as I normally do. I sat in the chair in front of his desk and made sure to pull my hem up enough to show my stocking tops. As we talked about a few mundane things like the weather and stuff, I crossed and recrossed my legs making sure he got an eyeful of what I was wearing underneath as I normally do in the morning."

"Finally we talked about the promotion. I uncrossed my legs and planted my feet firmly on the floor. My knees were spread and I told him that I want that promotion; I deserve that promotion. He agreed. I told him I wanted to thank him properly so I sat between him and his desk. I placed a foot between his thighs and gently crushed his cock with the sole of my shoe. He winced at first but then smiled and leaned back; I pushed a stiletto heel under his balls and into his ass. It ripped through the seam and I fucked his asshole with the steel spike."

By now, I had lifted my own skirt and was stroking my dick. Grannie had removed her harness and was fingering herself. Mom continued.

"He brought my other foot to his mouth and licked the bottom of my shoe. I stuck the point into his mouth and he gave my shoe a blow job. Finally I told him to eat my cunt. I spread my thighs, he ripped off my panties and dug his tongue deep into my hole. I mused at the fact he was sucking out my son's cum."

"He had an amazing tongue and made me come a couple of times, but it's not the same as cumming from a hard cock fucking me. Unfortunately he wasn't as big as you are Jer... Alison, but it was enough and he added his sperm to yours."

Grannie too needed a cock and was sitting on my lap with me inside her. As I rocked back and forth, I could feel Grannie spasm slightly.

"And he came and came and came. It was amazing how much he filled me up. I knew I wasn't going to be able to hold all of it in, so I made him eat me clean. He made me come at least five more times; I really lost count."

"When he was finally finished, his face was all slick and wet. I licked his cheek and gave him a light peck on the lips and thanked him again. He told me I should also go thank the CEO and VP who supported the decision."

"I had to straighten myself up a bit. It was a little embarrassing walking to the ladies with that just fucked look and my legs was a little wobbly too. After I fixed my face, wiped myself and recovered a bit, I went to see the CEO, Mr. Parker. The VP Ms. Vandyke was there too. It wasn't too long before I was kneeling naked on the rug floor and sucking on the CEO's big, fat cock while the VP was between my thighs and eating my cunt."

"I thought Mr. Cummings was a great cunt muncher, but Ms. Vandyke was incredible. I seemed to lose control of my whole body as I sprayed out like a fire hose. Then I was on top of Mr. Parker with his cock in my cunt; I felt something from behind. Ms. Vandyke had stripped off. Between her legs hung an uncut, hard six inch cock!"

Grannie moaned and spasmed again.

"She pushed it into my ass. Oh my god! I had never felt anything like that before. I came so hard and so many times, I blacked out. When I managed to regain my senses, I saw Mr. Parker being fucked in the ass by Ms. Vandyke. When she was finished with him, she moved between my knees and placed my legs on her shoulders before she pushed herself inside my cunt. It was so sore there, I still wanted it. She pinched my nipples hard and dumped her load into my belly. I came hard."

I came inside Grannie. Grannie had come so many times, she was flopping around like a rag doll. We both collapsed on the sofa. Mom's legs were spread so she could masturbate. She had come so many times, her hands were soaked and there was a pool of wet that sprayed in front of her.

After we all sort of recovered a bit, Mom said. "So that was my day."

Oh, congratulations dear. I always knew you could work your way up the ladder." Grannie said sarcastically. Then after a moment added. "After everything that has happened today and your promotion, we should all go out and celebrate!"

"What a great idea! They gave me a signing bonus too so it's my treat." Mom nodded emphatically. "Let's go to swanky place... Sewell's!"

Grannie laughed. "Sounds more like they gave you a couple of signing boners too!"

Sewell's is an extremely nice and expensive restaurant. I couldn't go in my boy clothes since they were too casual. Grannie and Mom insisted I should dress up like a proper lady. As Mom fixed my face and hair, Grannie picked out my attire and laid it out for me. They went to get ready and left me to change. The corset and panties were black lace with red trim. My new breast forms filled the cups perfectly. I slid the black opaque stockings up my legs and clipped them to a simple black garter belt.

The black dress was a tight body fitting, knit Vegas style dress. It had a modest vee neck with transparent mesh which was enough to show off my cleavage but hid the fact my breasts were not real. It clung to my bum and came down to mid-thigh. Bumps from my stocking straps and clips were obvious.

I looked at the shoes. They were beautiful and black and tall. Six inch stiletto spikes with open toes and ankle straps. They fit perfectly, but standing and walking in them was near impossible. Even after I followed what Grannie said about walking in heels, it was still a little wobbly. I pulled down the hem and stood in front of the full length mirror. "Wow, you look hot!"

I guess I said it a little too aloud. Mom gave me a wolf whistle and Grannie agreed. "If we weren't going to be late for dinner, I'd fuck you silly!"

Both Grannie and Mom looked incredible. Grannie wore a simple, blue, knee length, backless cocktail dress. The material was soft and her hard nipples poked out. Mom had to borrow something from Grannie. It was a red satin blouse; the top three buttons undone that showed off her black bra and a deep cleavage. The skirt was a simple short, black wrap-around. Both wore stockings and high heels.

"Ready?" Mom asked rhetorically. Grannie opened the front door. Suddenly, reality hit. I was about to go outside totally dressed and made up as a woman for the first time. I froze. They both assured me. "Come on, Alison. You look like a very pretty girl. I bet you'll turn everyone's head."

By the time I managed to get to the car, I was more comfortable with being outside. My strides became more confident especially walking in the tall heels. I loved the sound of my steel spikes clacking against the hard concrete and thought "No wonder women love wearing heels. It makes me feel so powerful."

Getting into the back seat of the coupe was an adventure; not that Grannie helped me any. As I ducked my head and stepped in, Grannie ran her hand up between my legs and backside. When I finally sat down, the hem had ridden up and exposed my panties. With the front seat back, there wasn't much room in the rear. My butt sank into the bucket seat and so my knees were higher than my hips. I kept trying to pull my hem down but not too successfully.

Mom and Grannie laughed. "Wow, what a slut! We'll have to show you one day, how to get in and out without any panty flashing... Unless you want to show off."

The drive to Sewell's was uneventful. I really couldn't make out the conversation between Grannie and Mom since I was in the back and was muted by the low rumble of the road noise. They were laughing and cackling about something. I just kept trying to pull my dress down.

When we arrived at the restaurant, I finally got my hem down enough to just cover my stocking tops. The valet opened the car door and helped Grannie out. The seat back launched forward and the valet extended a hand to me. "Miss, may I help you out?"

"He called me Miss!" I thought to myself. "He thinks I'm a real girl!"

I braced my left hand against the seat and took his offered left hand before stepping out. My legs parted as I placed my right foot on the ground; my hem rode higher and higher as I tried extract myself from the bucket seat. I tried to exit and keep my modesty at the same time but without any spare hands, I failed. By the time I was out, I was pretty much exposed from my hips down. I quickly pulled down my hem.

To his credit, the valet said nothing nor showed any reaction except for a large, noticeable lump in his pants. Mom gave him a generous tip. As we all walked to the door, Grannie took me by my arm and whispered loudly. "Alison, did you see the serious boner you gave that guy?"

Inside, we were lead to a small table. Grannie sat on one side and Mom on the other with me between. By the time I sat, my dress had ridded up again. My stocking welts and clips were showing. I was about to pull it down but Mom and Grannie prevented me from doing so. "Your Grandfather complained about the same thing when he always wore that outfit."

The busboy came over and poured our water. He noticed Mom's loose, open blouse and overfilled the glass. Apologetic and embarrassed, he scurried away. The manager immediately came over. "I want to personally apologize for the unprofessional behaviour. I want to ensure you that we will address it with him."

"Oh, no! Please don't do anything." Mom told him. "These things happen. It was an accident."

The Manager's eyes popped went he noticed what the busboy saw. Mom had popped another button. When she leaned forward, he could look down at her totally exposed her C sized breasts barely cupped by the shelf bra she was wearing. The Manager stumbled. "Err.. Uhh.. Oh. Okay, thank you. Please let me get you some complementary cocktails. I'll send a waitress right over."

"I bet he's sending a female over thinking she'll be less affected by your Mother's charms." Grannie said to me with air quotes. "I doubt it will make a difference."

The waitress came over. She was a pretty little thing; maybe five feet tall, blond hair pulled back into a long ponytail, pert little breasts but seemed to have amazing hips and bum hidden beneath the black skirt she had on. Her legs were strong and shapely. She opened and handed out some menus to each of us. "Good evening. May I take your drink order before you decide your meal?"

"I'll have a Rusty Nail, please." Grannie told her as she gazed at her menu.

"Hmm... Maybe a vodka Martini please." Mom followed with her order, then added in a little sassy tone. "And make it a little dirty."

The waitress was staring directly at Mom's large hard nipples which showed through the red blouse.

"And for you Miss?" The waitress then looked directly at me. Our eyes locked. There was a definite connection happening. She licked then bit her lower lip. "Um... Would you like something to drink as well?"

"What do you suggest, Miss?" I asked in my best falsetto voice.

"My name is Pricilla." She smiled her replied. "The bartender makes the best Margaritas."

"Okay, I'll try that!" I smiled back at here.

As she retreated to get our drinks, Mom turned to me and whispered. "I think she likes you."

Mom was always the flirt. She undid another button and pulled the front open. She may as well have been topless; she wasn't hiding much.

Pricilla returned a few moments later. She checked slightly as she looked at Mom's exposed breasts. Recovering quickly, she placed Grannie's and Mom's drinks down before she moved beside me and placed the cold Margarita in front of me. Her eyes fell to my exposed legs. Her thigh gently pressed agains my arm. "I hope you enjoy it."

"We're celebrating my promotion tonight. Please make sure our glasses are never empty." Mom suddenly told her as she lifted her glass.

"Congratulations!" We all clinked glasses. "Cheer!"

I gulped down half the glass. It must have been a double; I felt it right away. And my empty stomach didn't help any either.

Pricilla remained by my side. "Are you ready to order yet or would you like more time."

"Yes, more time. I think we need to order more drinks too!" Mom showed her empty Martini glass. Grannie swallowed the rest of hers. "Another round please, dear. Just like this one; it was perfectly made."

"Yes, I'll see to it right away." Pricilla scurried off.

"Drink up, Alison. You're falling behind." Grannie scolded. I finished the glass.

I barely put the stemmed glass down when another appeared. By the third round, my head was definitely a bit tizzy. Pricilla no longer pretended to accidently bump me. She stood beside me and rubbed her hip into me firmly. I'm not sure if it was the drinks or the fact I found her incredibly hot. I dropped my hand below the table and cupped the inside of her knee. She wore nylons which I assumed were pantyhose. She reacted slightly to the touch but did not move or protest. My hand crept higher and higher until it felt the familiar texture of stocking welts and bare skin.

Grannie ordered the rare roast beef. Mom wanted the Chateau Briand. "Chateau Briand is for two; with whom do you wish to share it?"

"Oh, yes. How silly of me. I forgot." Mom giggled. The drinks were having an effect on her too. "I guess I'll have the Beef Wellington. And shrimp COCK-tails all around!"

My hand had reached up and was rubbed her pussy through a small, thin thong. I snaked a finger under them and entered her hot, wet hole.

"Uh..! And for you Miss?" Pricilla asked me with a little quaky voice. "Are you ready... to... o..r..d..er?"

I wriggled my finger inside her. "What would you recommend?"

Pricilla bent over. Her face was next to mind. Her sweet, gentle fragrance filled my nostrils and mixed with the alcohol in my head. With one hand she pointed out a number of things on the menu, but with her other she laid it on my thigh. She played with my stockings and pushed my hem up even higher. Her hand pressed against my crotch. She looked at me; squeezed my crotch again and then her mouth gasped open as she pulled her hand back like it touched fire. "Uuuh... I uuh..."

I could see her mind racing to comprehend what she just discovered. I was afraid she was going to scream or something but then a wry smile broke across her lips. Her hand found its way back to my cock and rubbed it while she gave me some recommendations. "Personally, I like a big piece of properly dressed meat!" She told me. "I'd go down the double fillet mignon. And it's delicious!"

Pricilla rubbing made me so hard inside my panties and made answering a bit difficult. I nodded my head. She whispered into my ear. "Very good choice, Miss."

"Another round of drinks, please dearie." Mom ordered. "And a bottle of Champagne on ice!"

"Right away!" Pricilla responded as she pulled her hand away; reluctantly so did I.

There was a sheen of wet coating my hand. Mom grabbed my wrist and lick it. "Mmm... She tastes good. Maybe we should order her for dinner!"

The drinks had definitely affected me; both my head and my bladder. I needed to pee. I thought I was managing okay but I guess that's what everyone thinks when they become inebriated. Pricilla rushed over and took my arm. "Let me help you, Miss."

I looked at her and smiled as she guided me to the private rest room. There was no urinal; but there was a sanitary napkin dispenser and disposal bin. She took me to the ladies room. Pricilla stood me in front of the porcelain bowl. She pulled up my dress and pulled down my panties before sitting me down on the seat. She used her hand to make sure I was pointed downwards. I closed my eyes and let go. I gasped an "Aahh!" of relief as a stream of amber liquid splashed into the water below. Then a couple of Kegel contractions to get the last little squirts out.

I opened my eyes. Pricilla was standing right in front of me. I reached under her skirt to pull down her panties but found she had removed them. I pushed the hem around her waist. Her pussy was perfect and pink with a small trimmed soul patch of pubic hair. My tongue immediately went in for a taste. I used my tip and found her hidden pearl. Her clit was hard. I pressed against it and she came.

"Oh fuck! Yes, Miss! That's the spot!" Pricilla came again and cried out. I lapped up the liquid that leaked from her. "Oh my god! Your tongue is amazing."

She stood me up and changed places with me. My dress was still pulled up and my panties were around my knees. Due to all the drinks, my cock was a little flaccid. Pricilla took me into her mouth and rectified the problem. She held my ass and pulled me in as deep as I could go.

"Oh, Pricilla! You made me so hard!" I spasmed slightly. "I want to cum!"

"No! Wait!" Pricilla released me immediately. She stood and turned, then braced her hands against the toilet as she spread her legs wide. "Fuck me! Please Miss, I want you to fuck me with that cock of yours. Please!"