Gardening with Granddad Ch. 20

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The Big Day Part One - Jimmy's Transformation.
9.2k words
4.39
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Part 20 of the 26 part series

Updated 11/02/2022
Created 08/16/2002
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My Father tucked me into bed that just after midnight giving me a lingering kiss. I drifted off after our exciting pre-honeymoon night dreaming of what I might expect the next day.

When I awoke the sun was shining in my room and I heard noises from below where a large white tent had been set up in Granddad’s yard. It hid from view the preparations that were happening inside.

When I strolled out to the living room in my mini-kimono I was shocked to see the entire space had been set up to resemble a spa / dressing room.

From the kitchen cam a skinny tall bleached and suntanned man, “ Allow me to introduce myself, Carl, I will be your dresser, beautician and makeup artist for the day, here is your morning coffee, if you could have a leisurely shower we can get started, there’s much to do.”

“Thanks Carl, be right back,” I answered heading off for the shower.

When I returned Carl was preparing his tools – scissors, curling iron, combs, brushes and directed me to the makeshift barber chair.

“ Today Jimmy I will transform you in preparation for your wedding,” Carl said in his effeminate voice, “Your Grandfather has left very explicit instructions and he trusts you will allow me to fulfill his requirements.”

“Oh yes Carl, there is nothing I won’t do for today, ready when you are,” I exclaimed.

“ First, I need you to remove your robe and lie on the table I have set up. We will complete a full body wax which will cleanse your body of any hair that might still be present,” Carl instructed.

I stood and dropped by robe, clearly Carl was impressed with my ripped, toned and tanned teen body.

When I lay on the table he began removing the small amounts of hair that were present on my legs, balls, cock and under arms. The process was quite painless and quick, as my body is kept fairly well shaved.

He then asked me to return to the barber chair where he shaped and sculpted my eyebrows into a beautiful arch.

“Carl, they are gorgeous,” I squealed with delight when he finished.

“Thank you Jimmy, your Grandfather brought me in from LA you know, I am the best in this field and by late afternoon you will truly be a sight to behold,” he explained.

“Next Jimmy I need to add some color and highlights to your hair, this will only take about 20 to 30 minutes and while the color is taking hold I can do other work.”

“Okay,” I said noticing his cock head bobbing in his tight black lycra Mick Jagger type pants. Obviously this Queen was enjoying every moment of this transformation, as was I.

“How often do you do this Carl?” I asked.

“Generally, I take one client per week, but depending on timing and travel schedules I may take one every two weeks or two in some weeks if they are close by.”

“What exactly will you do for the rest of the day?” I enquired noticing it was still only 9:20 am.

He had finished adding the coloring and replied,” Well now Jimmy I will give you a manicure and pedicure.”

“Ohhhhh,” I purred, “I’ve never really had a professional do that.”

“Well I think you are definitely in for a real treat,” he smiled.

He took to working on my feet and toes sculpting and shaping each nail individually and very delicately. I noticed his nails were spectacular, long, shapely, polished and beautiful.

“Does anyone everyone ask about your nails or do you feel self conscience in public?” I asked Carl.

“At first I suppose I thought about it, but living in LA and having done them now for many years I don’t give it a second thought,” he offered, “and besides, Jimmy it really does tell men exactly who we are and what boys like us want from them now doesn’t it?” he teased.

“It does? I don’t know I have never really done this or thought about it,” I said innocently.

“Well, Jimmy I think maybe you have never done this, but I do think you may have thought about it and I do think given the situation here today you are probably fully aware of what we offer men and how much we like it,” he commented.

“Really, I don’t really know what is happening today and what you are going to do, I just know that I have been asked to make a commitment,” I said feeling somewhat sheepish about what was happening in my loft.

“Jimmy, your Grandfather explained everything to me, your relationship, the past year, last night, we can comfortably talk about today and your future,” he said calmly as if nothing was abnormal.

“You know, you know what is happening today, you don’t think there is anything strange?” I asked excitedly.

“Jimmy I told you this is my profession, I travel the US and around the world providing this service in very similar situations, and while there are some very, very different components to today, it basically is the same type of job I undertake every week,” he smiled, slowly rubbing and patting my hand.

I hadn’t even realized, he had finished my manicure now as well.

“You specialize in weddings?” I asked.

“I do Jimmy, but I specialize in very special weddings, weddings between a man and his chosen bride Jimmy, brides like you,” he said wheeling a small tray of polishes towards me.

“What do you mean Carl, brides like me?”

“Jimmy, there are many men who choose to take a bride that requires transformation like you. Every wedding needs a bride and groom and when there is a man like your Grandfather, who is very clearly the groom, I step in to create a beautiful exquisite bride like you,” he continued.

“But, Carl I really don’t understand I am not a woman and really not a bride,” I mildly protested.

“And that Jimmy is my job, to make you the bride you must become by 7 pm tonight,” he said picking up a bottle of polish.

“You mean that tonight I will be a bride?” I asked.

“Yes Jimmy you will,” he said shaking the bottle.

“A full complete bride, as in like a bride, as in woman?” I gasped.

“Finally, Jimmy yes you are beginning to understand why I am here, I would have thought you would know that given what your Grandfather asked you to do tonight.”

“But last night I thought was dress up, role play, just an act,” I said my pulse beginning to race quickly.

“It was dress up Jimmy and a dress rehearsal for tonight, did you enjoy last night Jimmy?” Carl asked with a gleam in his eye.

“Well, yes I guess I did, yes,” I answered.

“Then tonight Jimmy you will love even more, the work I will do today will not even compare to last night and after speaking with your Grandfather, tonight will not even compare to your playtime last night, now we need to do this,” he said opening the polish and placing my right foot in his lap.

He began painting each nail with a lustrous glittery pink polish. My toes were phenomenal, smooth, polished and a beautiful feminine pink. My foot rested on his bobbing cock, which made my cock spring to life watching my transformation, take place.

He then moved to each hand painting my fingernails in the same beautiful shade of pink.

“You transform boys into brides for a living?” I asked excitedly.

“Yes, I was slightly older than you Jimmy when I was a bride, there was no one to help and 25 years ago, this was not a talked about subject, so after I did myself, I decided I had the ability to help others,” Carl responded.

“You were a bride? Others do this?” I asked somewhat surprised.

“Yes, I was 22 and this is my twenty-fifth year and while there aren’t millions or even thousands there are many men who take young brides,” Carl explained, “ However, Jimmy there not many situations like yours.”

I asked him what he meant.

“Jimmy, I think you know there are not many brides who marry their Grandfather,” he offered,” and while some do role-play the situation it has never happened in reality that I know of.”

“But you said this was your business Carl,” I said questioning his previous explanation.

“Yes it is my business, but my business has always been older men marrying younger brides, it has never been grandfathers marrying grandsons, you are a very lucky boy Jimmy,” he smiled.

“I thought you said you were married though Carl.”

“I am married Jimmy, I am 47 and my husband is 81 now, but he is not my grandfather, “ he said, “ we are only the same in that I was very young and he was a father figure, there are many of us, though most do not publicly promote our relationships,” Carl said looking at me like an older brother.

“What you are doing today Jimmy is very special indeed and you have a very important and exciting future ahead of you,” he said softly, “ and we need to continue our work, so please get back on the table.”

“Wow this is more exciting than I ever dreamed it could be,” I said with the excitement of a bride-to-be.

“Jimmy, this next step is the most important and may make you feel the most uncomfortable, you need to remember though everything has been arranged by your Grandfather.”

With that, he picked up a large suitcase which he opened revealing a plush red velvet lining and revealing two 40 d tits.

“What the fuck?” I said bolting upright on the table.

“Yes, these are going to be yours Jimmy, your Grandfather selected them as they are huge for your gorgeous beautiful young body and they will create the illusion of an exquisite blond bride for him,” he said holding the first one in both hands.

“Relax please I need you to lie back down on the table Jimmy.”

“But how…”

He answered before I could finish.

“Each of these will be attached to your body using special theatrical glue and flesh tone cement,” he explained placing it on my chest, “ they will last about three days before you will need to remove them.”
With that he started applying glue and affixed each breast to my chest. When he finished he took flesh tone cement and built the breasts from my chest to the falsies. My shaved bald cock was standing fully erect while I admired my new huge tits.

“Jimmy,” said Carl, “ I think my work is making you very happy by the looks of things.”

“Ya Carl it is making me very happy and very fucking horny,” I smiled, “my fucking cock may never go down unless…”

“Unless?” Carl asked.

I stood fully naked in front of the full-length mirror admiring my gorgeous new physique.

“”Carl, I think for this amazing work you deserve a tip,” I said spinning around and placing his hand on my throbbing meat.

He wasted no time getting on his knees and swallowing my cock in his thick painted lips. The sight of this over tanned bleach blond old queen working my cock as I played with my mega tits made me shoot instantly.

“Now that was an unexpected tip,” Carl said licking the last of my cum from his lips, “ and now we need to get back to work.”

He put me back in the hairdresser’s chair and began putting enormous rollers in my long blond hair. He then had me sit under a dryer. Carl passed me a silver tray with joints and poppers and I happily took it indulging as my hair dried.

About 20 minutes later he lifted the dryer and put me back in the chair. He started combing and using a curling iron on my hair. About 40 minutes later he stood back and said, “Okay, let’s see what you think.”

“HOLY FUCK!” My eyes were riveted to the mirror. “FUCK!”

“Well?”

“Fuck Carl, it’s like my fucking grandmother’s hair!” I screamed.

“Yes, just like what your grandfather ordered Jimmy,” he laughed.

“Holy fuck Carl is that what he expects tonight?” I asked, “ he wants me to be my grandmother?”

“Now you’re starting to get the picture Jimmy, an exact replica, only younger and with one BIG BIG difference,” he calmly explained.

“ Oh fuck ya now I get it man, Carl get to work this is gonna be one fuckin wild wedding, grandma was one hot wild whore and I can match her, in fact I want to be even more than she ever was!” I ordered.

“That’s what I like to hear,” he smiled, “ so let’s get some makeup done before the tailor gets here.”

Carl set about mixing powder, gloss and applying it to my eyes, cheeks, brows, lips - I could hardly wait to see his work.

An hour later he turned the chair to face the mirror. I had been completely transformed. My face was now perfection, it was flawless, I was spectacularly made up.

A knock came on the door. Carl hollered come up Trevor.

Into the room came this tall slim dark skinned Latino, the mirror image of Carl only the darker version. I thought fuck another queen!

He had a large white box and three garment bags.

“Okay, Jimmy,” Carl said, “we need to take a break so that Trevor can do your final fitting.”

“Fitting?”

“Yes, Jimmy I have your ensemble for tonight and need to make sure it fits perfectly,” Trevor lisped.

He had me stand on a wooden platform and took from the box the tiniest sheer thong I had ever seen. He explained it was designed to completely flatten my cock and balls and make me look flat I put the thong on and was mesmerized by how my whole body was now flat except for my tits.

“Excellent Jimmy,” Trevor remarked it fits perfectly, “now we need to try the gown on.”

Trevor opened a garment bag and removed what looked like would fit someone half my size.

“Um Trevor, that will never fit me,” I suggested.

“Oh I think you’ll find differently Jimmy,” Trevor replied helping me step into the neck of the ultra sheer coverlet.

The outfit was long sleeved and fit like skin over my arms. The neckline was scooped so low the fabric came to just under the top of my nipples. The floor length gown clung to my body like plastic wrap. It was formfitting over my ass, tits, legs and newly flattened cock.

“I think it’s awesome,” I squealed so pleased with Trevor’s creation, “except it may be too long.”

“Not so fast my friend,” Trevor laughed, “I wouldn’t get that wrong.”

With that he pulled from the box plexi-glass see through 9-inch stilettos putting a slipped on each foot. I was spectacular.

“We just need to adjust the length of the arms and it will be perfect,” said Trevor helping me out of his creation.

I was standing on the box and removed my thong, which left me standing naked in front of Trevor and Carl wearing only my fabulous kinky high heels.

“My, my, my, you are a beautiful work of art Jimmy simply breathtaking,” Trevor gasped, “tall, muscular, incredible huge tits and a spectacular monster cock, simply stunning Jimmy.”

“I couldn’t agree more Trevor,” chimed in Carl, “ he is our best creation ever!”

I loved being exposed on the platform in front of these two makeup queens. Their cocks were bulging from their tight form fitting pants. My cock had sprung to life once again and I began posing front on and back on in my sexy plexi-glass heels, two-foot high blond beehive hairdo and newly grown massive man tits. I had become what my grandmother must have been like forty years ago. If she had been blessed with a huge boy cock.

“I think we need to release some more of that tension Jimmy,” Carl leered, “ what do you think Trevor?”

“O my god Jimmy, would you let us?” Trevor was quick to ask.

“Only if you join me naked Trevor, I think we need to have some pre wedding fun!” I laughed.

With that, both men shed their clothes. They were both as smooth as silk, not a hair on their bodies. Both men were exceptionally slim and had hourglass figures. I guessed most women would kill to have bodies like theirs. Both men had flawless makeup, discrete yet highlighting their features, along with pierced ears. Their hair was coiffed to perfection and if they didn’t have cocks and they could have easily have passed for flat chested women.

Carl was the first one on my cock, licking it with his tongue between his painted hungry lips. Trevor went to work on my smooth cum filled balls. As Carl had already experienced my thick load I wanted to see him enjoy my tight tasty ass. I guided him around to my hard muscular bubble butt and bent over slightly to allow his tongue into my crack. He wasted no time exploring my tender hole and spreading my ass open for his pleasure.

Meanwhile, Trevor had moved upwards onto my cock. It was bobbing in his mouth as he eagerly slurped on my throbbing meat. This scene was ecstasy standing on a platform in front of full-length mirrors being worshipped by two aging beauty queens. Then I felt Carl’s cock touch my hole that had been moistened by his mouth.

“Baby, you are gonna be fucked for the first time as a woman!” he whispered in my ear, “and your grandfather won’t have the pleasure of busting that cherry either, it’s all mine.”

And with that he thrust his cock into my waiting cunt. Fuck, it was amazing to have these hungry fag men, one using my ass and one using my cock for pleasure.

“Trevor, fuck you have to come feel this,” moaned Carl, “ this is the finest piece of boy pussy you’ll ever fuck.”

Trevor was off his knees and behind me in a flash watching Carl’s cock slide in and out of my begging ass.

“Fuck me Carl, please fuck me, fuck your beautiful new creation,” I screamed, “ own the pussy that you made please Carl fuck me!”

He pushed me from the platform over to the massage table where he bent me over exposing my ass for his viewing pleasure.

“Oh ya baby Carl is gonna fuck your pretty girl pussy, Carl is gonna breed that cunt with all his cum.”

“And then baby, I am going to eat your ass filled cum load,” said Trevor.

I looked back to watch this crazed bleach blond girly man fucking my ass. It was such an amazing sight.

“Trevor please bring your cock to me,” I asked in a new feminine voice.

As he stood in front of me I wrapped my pink painted lips around his shaft and began working his smooth girly cock into my waiting throat.

“I bet you never thought you’d be a beautiful bride did you Jimmy?” questioned Trevor, “and I bet you never thought your own bridesmaids would be fucking you on your wedding day either?”

FUCK! This was so hot. I had no idea they were my bridesmaids. Here were three men, now transformed into hot boy chicks going at it in a wild three-way.

Trevor’s cock erupted in my mouth. I drank every gob of his bitter cum. Then, Carl’s cock burst in my pussy.

“Fuck baby take my load, let me see it run down your smooth waxed leg baby,” he ordered.

I rode his cock until every drop of cum had been emptied into me. God, I was so glad we had five hours to go. There was still time for more fun.

We enjoyed a glass of champagne, smoked a beautiful big joint and giggled like schoolgirls.

Trevor said he had several more surprises in his bags. He zipped another garment bag and took out hangers with a huge selection of post-wedding and honeymoon outfits.

“Oh Trevor these are absolutely gorgeous!” I told him, “ I have never seen such designs they’ll be perfect.”

“Yes, I know, you have the perfect body Jimmy,” Trevor answered, “ your ass makes everything I design look even better and you are tall and ripped and show off every asset so well.”

He then explained that as the evening progressed, he would be changing me into various specialty designs to match the changing theme.

The designs were made of mesh, sheer, crocheted, lace, chains, leather and a variety of other wild fabrics.

Carl interrupted, “Okay, Jimmy I need to do more work right now, back in the chair.”

He took a piercing gun in hand and pierced each of my ears.

“We should have done this a few weeks ago, but we wouldn’t have wanted to spoil the surprise,” he grinned opening a plush black velvet box.

Inside were the most phenomenal diamond necklace, earrings and bracelet imaginable. The drop earrings were like miniature chandeliers and the bracelet thick and covered in diamonds. However, it was the necklace that drew gasps. It was tight fitting to the neck but dropped 8 inches in a dazzling display of magnificent stones. Carl affixed the earrings and bracelet, finally placing the necklace around my neck. It ended just above my humungous man tits.

“ Carl, that is unbelievable!” I exclaimed, “it must be worth a fortune!”