Vicki's Story Ch. 01

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A young man on a personal voyage of discovery.
13k words
4.59
11.7k
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Part 1 of the 8 part series

Updated 03/08/2024
Created 01/28/2024
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Cagivagurl
Cagivagurl
3,547 Followers

A quick note to credit the people who helped with this story. The story was written for Vicki. It is really her creation. I need to thank also Tim, for all his help with editing.

Note to all. This is a work of fiction. All characters indulging in sexual activity are over the age of eighteen.

Chapter One:

She started unbuttoning my shirt, followed quickly by my jeans, which she tugged until they were around my ankles. Right at that moment, I felt the deepest embarrassment I had ever experienced.

I wasn't expecting sex on a first date, I mean who does that? Right?

Underneath my jeans, I wore my little silk panties and a pair of sheer nude pantyhose.

When Patrice saw them, the shriek was ear splitting. "What the fuck dude?"

It rocked me to my core. The embarrassment and shame raged within me. The question remained. How did I get to that place in time....

*****

I grew up an only child. Not looking for sympathy. I would have enjoyed siblings, but then I wouldn't be me, or maybe I would. Who knows.

My father was a workaholic, which meant we never had what I would describe as a close relationship. My mother, although she was a stay at home Mom, had her own life. God knows how many charities she sat on or chaired.

She saw it as giving back.

Weekends, I spent with my grandparents. I know that sounds shitty but mine were different. I didn't hate it, I loved it.

"Holy smokes, Fran. God damn it boy, that woman still drives me crazy."

Following his eyes, I watched Gramps gawking at my grandmother who was working in the garden with us.

"What do you mean Gramps, I don't understand?" I replied

"One day Fran, you'll get it. Your Nan is a gorgeous woman is all I'm saying."

He didn't have to tell me that. I knew it already.

Their house in Bedford, Shaker Heights, was a veritable mansion. A huge sprawling place, that backed onto the golf club, my favourite haunt while I visited.

I mean, it didn't start out that way, but it was Gramps who sort of encouraged me. I remember asking him if he would buy me a new book.

He glanced at me as he rubbed his chin. "Fran me boy. If I buy that for you, it will mean nothing. If you work for it and earn the money, it will mean a hell of a lot more to you."

I absorbed his words before replying. "Do you have any jobs I could do?"

"That would be to easy Fran although, might I suggest something?"

"Yes, Gramps?" I replied eagerly waiting for his response.

"I notice you walking around on the golf course a fair bit. Do you ever find any golf balls while you're strolling around?"

I knew exactly what he meant, and it was his way of encouraging me to be self reliant.

Shaker heights, was the old money part of town. My grandparents were very wealthy. Gramps, and Nan as well, had worked very hard for their money, and had accrued the benefits by retiring early.

I loved my sleepovers with them, mostly because I got to sleep in my own enormous king sized bed. The golf course, quickly became my favourite hangout

I developed a burgeoning little business finding and selling lost golf balls to the players.

Gramps was pretty smart cookie though. "Fran me boy. How many of those golf balls were actually lost when you found them?"

"Some." I replied guiltily.

"Yeah, okay then, remember this Fran. Some golfers mark their balls, be god damned careful which ones you find." Turned out to be good advice. Those ones I kept for several weeks before taking them to the Clubhouse to sell.

The house was cool, but it wasn't the only reason I loved to visit Nan. It was her... I loved to just hang around with her. She was every boy's fantasy. She was movie star gorgeous. Even the sexiest models would have been jealous of her incredible good looks and stunning figure. Even to a besotted young boy she exuded confidence and a magnetic appeal.

I'm sure she knew about my crush. She did seem to almost flirt with me. I heard Gramps telling her off one day. "Don't tease the boy. For god's sake, you're his grandmother. That boy is already obsessed with you."

"Stop it Frank, Fran and I were just having fun."

"Fun my ass, the boys walking around with a friggin boner half the damn day."

There were of course other benefits to staying with them as often as I could. The house was always filled with celebrities and dignitaries.

They had so many parties and gala events. Nan, like Mom, loved to work with charities doing fund raising.

Nan was awesome, everybody fell under my her spell. She definitely was sought after.

Regardless of what she was doing I was always, right there on her tail. She dragged me on shopping trips and expeditions that took all day. Our escapades always included lunch at the most up market restaurants. Regardless of the time there was always a table for Nan. No reservation required.

We were treated like royalty. Whist we shopped, she made me help her choose dresses or shoes, which was always accompanied by a little fashion show. Shoe shopping...damn, those were my favourites. I practically pushed the assistants out of the way as I helped her try on every pair.

"Are you sure you want to go shopping with me Fran?" I sensed a guilt in her question.

"I love our expeditions Nan. Of course I want to."

I loved to kneel down in front of her and help her slide them on. Glancing up those long sexy legs trying for the tiniest glimpse of panties.

Her legs were magnificent and always covered in the highest quality stockings or pantyhose. At the time, miniskirts were all the rage and although she would be described as mature she carried it off with ease. She had those glorious long sexy legs which never failed to draw attention from men, women or me either, for that matter.

She could be a real tease, a woman who loved life and enjoyed the better things life had to offer. She knew she was attractive and she loved the attention. She could have been a model, in fact Gramps told me she was courted by some of the top agencies in the world, but decided on a life in the world of business. Finance to be precise. She found that so much more exhilarating than the shallow world of fashion. She loved fashion but I remember her words when I asked her why she chose her path.

"Fran, I want to be remembered for more than my looks. I love the attention but I want to do something substantial with my life. I want to look back on it proudly."

Nan and Grandad used to host huge parties. On those nights, the house would be overflowing with the local glitterati, celebrities, movie stars and even a couple of senators. Nan used to work in high finance for some of the biggest firms. She was definitely the hostess with the mostest.

She was an amazing woman and I wasn't the only one who thought so. Regardless of the party theme, she was relentlessly followed around by a swathe of admirers with their tongues hanging out.

Even some of the most notable celebrities were as beguiled as me. When she set her mind to it, she could captivate anyone. Her truth was Pop, she loved him deeply and her band of obsessed admirers were never more than that. She only had eyes for Gramps.

Gramps had his little secrets as well, like the still he ran in his workshop. He made all sorts of alcoholic hooch in there. He had bottles of all sorts stored. As I got older, he allowed me to share a little drink with him.

Once Grandad passed, my visits seemed to take on a much larger importance for Nan. The house was still full of people. She had her share of suitors and I hated each and every one of them.

They got to take her out to all of those fancy restaurants and events. The newspapers' society pages were always filled with photos of Nan at different events. Even as she got older and retired, she never lost her innate radiant beauty.

In her later years she lost some of her vibrancy but her beauty never faded. Men still chased after her although she never seemed to take up any of their offers. She loved the tease but I think her heart belonged to only one.

Our relationship grew closer and I think my visits even became a highlight for her. I became the centre of her universe. She always made sure we had wonderful dinner parties although, just the two of us most times. She was a wonderful cook and the fact she let me drink champagne with her didn't hurt.

Nan missed hosting those huge parties, they were her passion. When I stayed over she was able to host a few parties. She taught me how to dance, there was nothing more wonderful than being held in her loving arms as we glided around the living room to the sounds of count Basie's orchestra.

Nan had a huge influence on my life, in so many ways. She was in her late fifties, most though would never have guessed. People, if asked, would have guessed her to be much younger.

As she moved into her sixties, she suffered poor circulation. I used to feel guilty sometimes when she had been spending hours running around after me. I could see the pain as she relaxed back in her favourite armchair. Trying to be helpful, I slipped off her slipper and gave her foot a little rub.

The effect was instantaneous. Nan sighed deeply. "Oh my! Francis, that feels so nice."

I sat up on my knees rubbing in earnest. The surge of excitement coursing through my veins elevated me to new levels. The feel of her nylon stockings felt so stimulating. As I rubbed and squeezed her feet I noticed the aroma. It was earthy and enticing. I removed her other slipper and gave that one a rub as well.

She always relaxed entirely and moaned contentedly. "Oh Fran, that is absolute heaven."

She made sure that I knew she enjoyed it with other little moans and sighs of pleasure. Using the thoughts and recollections from the day's events, my mind conjured up intimate little fantasies. Those fantasies became mainstays throughout my formative years.

That little foot rub became a daily ritual. I especially loved when we had walked home from the shops. Nan, being somewhat of a fashionista, still loved to wear heels and stockings. God that was my favourite. I loved to slip off her heels and give her the foot rub she loved the most. She always said that she could take off her hose and shoes but I argued she just needed to sit back and relax and let me work my magic. I know Nan felt a little strange about the foot rubs because she never let me do it if there was anyone else around. She definitely didn't tell anyone, especially Mom or dad.

My obsession with Nan's hose shifted a little as I got older. I, of course, had my list of chores when I stayed at Nan's. I mean that's the reason my folks were so keen for me to visit and stay over. I mowed the lawns and did the gardens. With Nan's help of course, she loved her garden.

Nan never said as much, but it was so obvious, she wished I was her "granddaughter". I definitely felt loved. Never once did I see that as a rejection of me personally. There was just a different type of bond between a grandmother/granddaughter. And at different times, that shone through. From her painting my nails (which I loved!) to the almost "spiritual" task of teaching her "granddaughter" to walk in heels. So of course when she came home with a new pair of Versace', I was there to wear them first.

Some might say she used me. The reality was much different. She knew I took first rights to wearing them but I don't think she fully grasped how much more there was to it. I loved more than just wearing them. It was as much the scent of her worn heels and nylons and boy, that impacted me.

Even today, those smells, that strong earthy scent, still lives strongly stored forever in my neuron pathways.

But, as she got older, I started to do other things as well. I took over the laundry. Not just because I had to, I wanted to, and it was completely selfish. I loved washing her stockings. I used to wash them by hand, careful not to put any ladders or runs in them. It meant I had plenty of time to slip them around my neck and face. Drag them sensuously across my skin, breathing in the earthy pungent aromas. The tiny electric shocks tingling for hours afterwards.

Once they were washed I liked to sneak them into bed with me rubbing them all over my body before sliding them up my legs. I loved to lay in bed with them pulled up high. I loved the feel of her most precious silk pairs, the really expensive ones. I loved the feeling of my hands running up and down my legs, feeling the slinky silk slide deliciously over my skin. The feel of stockings is something that has stayed with me throughout my life. Even after I went off to college.

Once, Nan's shoes actually fit me. Well...that opened up a whole new world.

Nan used me to break in her new shoes for her. Late at night when the house was dark I used to pull on her stockings and my favourite pair of her heels, which were her black patent leather work pumps.

Not the cheap plastic kind found today, but real leather which only added to that wonderful tapestry of my fantasy world. Images of her painted toes and fine nylons filled my mind. It wasn't just her new shoes I loved to wear, it was the old ones, her favourites. The scent her shoes generated, when her pretty feet sweated throughout the day, every day. Week, after week, after week. I was quickly becoming addicted to that scent.

Nan used to love showing me through her old photo albums and talk about the outfit she was wearing. She talked endlessly about the designers and the styles and which ones were her favourites. Slowly and unintentionally, she drew me into her world. Even though she was into her sixties, she still looked elegant and she maintained her interest in fashion.

The house was always filled with magazines and the clothes she wore were never what you expect a grandmother to wear. Even then, she loved her heels, although she never wore the tall steepling ones. Her wardrobe was full of fabulous clothes and shoes. I don't think she had ever thrown anything out, which was perfect for me. I had a wonderful collection to choose from and try on.

It was my guilty shameful obsession. I loved to put them on and play dress up in her clothes. I loved the feel of the beautiful silky fabrics which were so soft and smooth. The more I dressed, the deeper my compulsion ran. I loved it. There were towering heels from her younger years that really tested my balance. There was also the bulging drawer full of my favourite lingerie she didn't wear any more so, she never missed the ones I took.

The lingerie was heaven and overpowered me. The shoes I adored...preoccupation? No. It ran far deeper than that. It quickly became an addiction.

I cherished every piece, the textures, the shimmery glow. The feel of a silky a baby doll lacy chemise, as it caressed my skin. The feel of a sexy pair of silk panties. Heaven, it was pure luxury.

One day we were sitting side by side, looking through her old albums, I sensed the melancholy. She missed those parties. It drove me to say "You should have a party Nan."

She glanced at me, a warm smile spreading across her face. "You're right Fran, we should. Will you help me?"

"Of course, I would love to." I gushed.

She gave me a big hug and started planning. "Francis I really will need your help. Its time this old house had some fun. We will make it a fundraiser." The smile on her glowing face showed how much the idea excited her.

Nan went crazy as she planned. She sent out hundreds of invites, all handwritten on the most exquisite custom paper. It was to be a black tie event and she was determined it was going to be the highlight of the Cleveland social calendar.

The night of the party arrived and the place was crazy. It was full of caterers and guests. As the guests arrived, it was my job to meet them and guide them in and introduce everybody.

My little heart did a flip as I was welcoming guests. There, walking up the steps towards me, was a goddess. It didn't hurt that I was wearing a pair of satin panties and sheer stockings under my suit. Oh my god my heart fluttered and my mouth went instantaneously dry. She was tall and graceful, possibly about my age, eighteen?

She walked right up to me with her seemingly endless, long, silk covered legs. She wore a silver ball gown with a split all the way to her hip and as she walked it flowed openly exposing those gorgeous sexy legs which were perched precariously on what must have been four inch, needle point, silver chrome heels.

Open toed, they displayed her beautifully shaped, red painted toes, which peeked out sexily. My eyes drifted up her gorgeous, taffeta covered body. The neckline was low cut and she was obviously braless. Her nipples were like little diamond peas pushing out through the lacy fabric.

I was tongue tied and nervous. She stood right in front of me. I was supposed to guide her inside and introduce her. Unfortunately, I couldn't move, my heart raced, my palms clammy.

Truth be known, I'm not sure if it was her or the fabulous gown and shoes she wore.

She peered down at me. "Well, I am waiting." She moaned impatiently. "I am Constance Gifford."

I stumbled my way through a hello and led her into the front room. She stood beside me taking it all in. "Get me a drink will you." It wasn't a request it was an order. I slipped away to get her a glass of champagne. When I returned, she was standing, talking to Nan. As I approached she took it without even acknowledging my existence. I saw the look of displeasure wash over Nan's face as she saw me blushing. She leaned down and kissed me on the cheek. "Francis darling will you be a love and get some nibbles for us?"

I rushed away to get the food. My time that evening was taken up chasing after all of the guests and in particular Nan. As attracted as I was, I tried to give Constance a wide berth but she seemed on a mission to make my life hell. It was like I was her personal slave. As uncomfortable as I was, I put up with her rude behaviour, just to bathe in her presence. Besotted I was drawn to her. Her aura totally overpowered me.

With the party in full flight I flipped from guest to guest, ensuring they had everything they wanted. As I moved around, I overheard Constance, talking to another young girl. "This party sucks and that dour old woman! I mean god who does she think she is?" They both giggled before Constance added. "She may have been something when she was young but now, god, she is just a withered up old prune."

My bubble burst. If she had been a boy I would have punched her there and then. I refused to do anything for her after that. I completely ignored her.

Nan, of course, picked up on my mood. "I am sorry about Constance dear, she can be a bit overpowering. She is very beautiful, unfortunately, it seems to have gone to her head."

I never told Nan what Constance said. It would have broken her heart. I did however harbour a very deep resentment and I hoped one day I would have the opportunity to tell her what I really thought of her.

It was those early years that fuelled my strengthening desires and defined the rest of my life. I loved playing dress up late at night when Nan was fast asleep. I luxuriated in walking around wearing her lingerie, her stockings and high heels. It was fast becoming the highlight of every day. As Nan went off to bed, I was drawn deeper and deeper into my new world. If Nan was late going to bed, I got itchy and nervous. My expectations growing quickly. It was almost a relief when she finally went to bed and I could rush upstairs and feel the eroticism of my dress up game.

I wasn't a jock. I wasn't into sports at all, apart from my beloved baseball. Nothing else interested me. I was physically less than average, my one redeeming feature; my legs. I loved my legs. They were slender and shapely. I loved walking in Nan's shoes. I spent hours in her heels just so I could stand in front of the mirror. My ass stuck out, hands on hips, striking a models pose.

Cagivagurl
Cagivagurl
3,547 Followers