When I was a kid any time off my parents got was spent at our timeshare. Even on it's worst weather days it was twenty degrees warmer than home.

Ours was at the end of the row of timeshares, next to the privately owned condos. Those places had their own driveways, and garages, they almost looked like individual homes. That is where Damian lived. He was a local lawyer and liked to invite my dad over for beers and hoops in his driveway. Over the years we joined him for holidays if we were in town. My parents would even make special trips to be there, if possible, for special occasions. He was our closest family friend.

I met him for the first time when I was still an only child. We were having some family beach time and I noticed my dad talking to a man that seemed impossibly tall, with dark brown hair and matching eyes. He was thin but seemed very big, he smiled a lot and was younger than my dad but seemed just as smart. I was mesmerized by him, he was like a Disney prince with a dash of villain, and I watched him the whole day.

It was getting late and was time to pack up our stuff to head back to the condo. My mom and dad were chatting with Damian and I wondered up.

"Scott, it was great meeting you and thank you for introducing me to these two beautiful ladies," Damian said and smiled down at me.

I was only nine and swooned. Damian had this affect on any person that enjoyed the company of men. He was always full of compliments, it made his dates very jealous. I watched many different women struggle with their jealousy to remain in his good graces through the years, it never stuck. Damian loved to pick up the underdog, take the lonely girl at the party for a walk along the beach to pick up her spirits, even at the cost of his date. Getting angrier, waiting for him at the business along the beach that is trying to close up and is kicking her out.

There was one such incident involving me, it was the night of my high school prom. I was not popular, at all, no one knew I existed even. I wasn't as thin as the other girls in my school. They didn't have any curves, and were slim, I was the opposite. Not only did I have boobs and a butt, but I never lost the baby fat around my middle. I was also a creative kid, loved acting and art, I was pretty and had curves but I still gave off a weird girl vibe which negated any of those positives. No one asked me, I was not going.

My parents felt terrible so they allowed me to invite some friends to drive with us to the timeshare to have a beach party there and stay the weekend. By the time the weekend came all of my friends had prom dates so I went alone with my parents. I was finally eighteen years old and instead of heading to prom I was in a car with my parents, brother and sister.

We arrived and I headed straight for my room. It was time for an epic depression nap, hopefully to last all weekend. Mom and Dad were heading to Damian's for dinner with the brats. Even the prospect of getting some post eighteenth birthday flirting in with the flirt master himself couldn't pull me from my pity bed.

I guess my dad relayed my sad story to him because Damian texted his girlfriend, cancelling their date and formulated a plan. He arranged with my mom to take me shopping in town the next morning and to pass along a message.

"Be ready at 7pm sharp for an evening of dinner and dancing. Dress is cocktail formal."

My mom told me the plan when I woke up the next morning, and that did the trick, depression over. I got dressed and she took me to the vintage boutique in town. They sold dresses from the 1920's through the 1980s, mostly cocktail and prom dresses. I found a vintage 50's cocktail dress, navy blue velvet off the shoulder bodice with navy blue mesh skirt that went just below my knees.

I was dressed with my hair and make up done by 7pm, just as I finished the doorbell rang. Damian was dressed in a perfectly tailored black suit with a dark purple shirt, skinny black silk tie, and black vest. He wore gold cufflinks and a black, purple and gold pocket square. He was the most flawless man I had ever seen. For the first time since I met him he looked at me like I was a woman, surveying my person from head to toe. His eyes stopping at my cleavage, my breasts straining against the tight velvet holding them in and up.

He looked me in the eyes with a smile and said, "Well, are you ready?" and held out his elbow.

I hooked my arm through his and let him lead me to his car.

We drove in silence, I was nervous and I didn't even care where he was taking me, I was just enjoying the way he smelled, and the beautiful drive. After a thirty minute ride we arrived at a restaurant that looked like a small plantation house. They served gourmet cuisine and featured a crooner and a small band, with an old fashioned dance floor. The night was magical, dinner was delicious and I was able to loosen up with a couple glasses of wine.

After dinner he taught me how to waltz. I really enjoyed it, being swept around the floor in his arms. Then a more exciting beat started and he told me it was the Tango. He pulled my hands up, which pulled me to him, our chests pressed together sharply. He smiled, turned his head, putting his cheek against mine.

"Relax, let me lead you," he whispered in my ear.

My body was still buzzing from his lips against my ear and now he was grabbing my arms, occasionally a leg, and wrapping them around his body as he moved me around the floor with him among the other dancers. As the song came to a close he bent me backwards, one leg between mine, in a deep dip, that lingered and allowed me to feel a bulge hardening in his pants against my stomach. As he pulled me back up I drove my hips against his bent leg, I could feel the heat of his knee and then thigh through my panties. Before a scene could be made he pulled me the rest of the way up and called it a night.

When we got into the car and headed home neither of us said anything. I couldn't stop thinking about our last dance. How his hands felt so good on me and his thigh felt so delicious rubbing against my pussy, if only for a few seconds.

"I could not believe how grown up you were when I arrived tonight. I just wanted to make a kid forget about her prom, give her a good memory, but I ended up with a pin up girl that knows her vintage cocktail formal," Damian said, breaking the silence.

His hand found its way to my hose covered knee while he was talking, and I could feel a vibration through my entire body. I was beyond thought, I was hormones, nerve endings and need. I realized he was waiting for me to answer a question.

"What was that?" I asked in a daze as his hand squeezed my thigh, it was a little higher.

"I asked if these were thigh highs or pantyhose."

"Oh, they are pantyhose," I answered honestly.

I looked at his profile and saw a strange reaction, he looked both happy and uncomfortable with my response.

We both grew silent, his hand roamed up my thigh and began to venture from the top to the inside, I was slowly spreading my legs wider, without realizing it. I was soaked through my pantyhose, and I just wanted him to touch me, put his fingers between my lips and play with my pussy. I knew how to give blow jobs, I had given a few and was always told that I was spectacular at it. Looking at his lap, the bulge in his pants made my mouth water. I did not have the confidence to tell him, to go after what I wanted. So I laid my head against the back of the seat and enjoyed his roaming hand, hoping he would finger me and push my head down to his lap to suck his dick. It was seconds after this thought that I felt his fingers brush against my pussy lips over my thin pantyhose.

"There are only nylons here, no panties Georgia, and they are getting very moist, right here."

As he stated the last two words very bluntly he ran a finger tip from the top of my slit just inside my pussy lips, over the hose, to the bottom. I moaned and grinded my hips against his hand.

"Oh shit, you are very wet, little girl. We're going to have to pull over so I can make you cum."

He was rubbing two fingertips just inside my folds applying more pressure this time, but pulled them out so he could steer us off the road. We were actually pulled off the side of Damian's driveway, just across from our timeshare.

He killed the engine, pushed my skirt up to my waist, and pulled my knees apart. He began pushing the hose between my lips with one hand and rubbing from clit to pussy hole with the other. I pushed his hand harder against me, needing more friction, wanting to feel his flesh against mine. It was like he read my mind, and I felt him tugging at the crotch of my nylons and soon I heard a ripping noise. Then I felt his finger tips with no hose in the way. His bare fingers against my clit, rubbing my wetness around the inside of my lips avoiding my clit again and again only to run a stiff wet finger over it quickly, and circle it again and again. My legs began to tremble. I clutched at his shoulder, feeling my first orgasm wash over me, I was shaking and moaning.

He was saying, "Oh yeah, that's it, cum for me, cum all over my hand!"

I finished shaking, he smiled and wiggled a finger against my clit, making me cry out.

Then he laughed and said, "Oh is that a little sensitive?"
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Pub: 03 Jan 2021 08:13 UTC
Views: 171