A Bareback Rider – Pt 02 Deborah

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by Cristiano Caffieri

The one great thing about being a writer is that you can write yourself into any story, make love to the most beautiful women, live any lifestyle you please, you can even be a time traveler if you so desire. That’s what I’ve decided to do, write myself into a continuing story where I delve deeply into my past and make it a lot more interesting than it really was. The women who ignored me, rejected me and embarrassed me better watch out – I’m cumming for you!  

The Story Begins

In my teens, I lived in quite a small village around five miles outside the city. The most outstanding feature of our tiny community was the sprawling mansion owned by a family who squired much of the surrounding area. The eldest daughter of this illustrious household was named Deborah. She was an absolutely stunning girl, impeccably dressed and with a smile that could charm the birds out of the trees.

She’d occasionally walk through the village with her two dogs but she didn’t have much time for us peasants. When she did speak to us it was in a patronizing tone, much like you would talk to a pet or a halfwit. However, now she’s going to be a part of my story – things are going to change.

I was under 18 when I last saw her, she was certainly not interested in me then and I knew that she wouldn’t be interested in the same scrawny young guy with a baby face now.  Consequently, I decided for this time travel adventure  I should be around 25, well turned out and the owner of a fancy car, possibly an Alpha Romeo.

During my last few months in the village local gossip had it that she was banned from driving by her father because she’d smashed up a brand new MG he’d bought her. Poor Deborah had to travel to the city by bus and actually mix with the lower classes.

It was also common knowledge that she was going to study fashion design with a famous couturier in Milan and was taking Italian lessons at technical college in the evenings. My new shape-shifting, time traveling persona immediately signed up for the same class. I already spoke a bit of Italian as that was my father’s heritage but I didn’t speak it well.

Immediately I entered the classroom I made it my business to approach her. With my well-tailored suit and educated accent she never suspected that I was the broad spoken wretch she’d seen in the village occasionally, although she did that say I looked familiar.

I must have made a good job of my transition because she seemed to take to me right away, and when I offered to drive her home after class she accepted without a moment’s hesitation. When she saw the car she was most impressed, and I foolishly asked her if she’d like to drive. Once outside the city, she flew along like a bat out of hell. It was pitch black and the road was full of twists and turns but it did not persuade her to ease up on the gas pedal.

When we arrived at the house she asked me if I wanted to come in for a drink and I  was only too pleased to accept her invitation. However, we didn’t go into the house, she drove around the back and then led me up a stone staircase to a games room above the stables.

“This is where my sister and I hang out,” she said, as she opened up the door.

It was quite a place, there was a pool table, a table tennis table, weights,  a shuffleboard court and a massage table. We walked the length of the room to a little cozy corner where there some comfortable wingback chairs and a cocktail cabinet.

“Is Scotch alright?” she asked, but before I could answer she opened up the cabinet and poured us two drinks.

“We used to spend a lot of time up here when I was young,” she told me, “my cousin Freddie used to come for a couple of weeks every summer and we’d play strip billiards.”

“That sounds interesting,” I replied, my glass shaking in my hand just thinking about it.

“I’ll play you a game if you’re up for it,” she laughed, “but I’m good, darn good.”

Preferring to play table tennis, envisioning her tits bouncing up and down, I put forward the suggestion saying I’d never really played billiards. She looked a little unsure but then said, “Why not,” and we chose our bats and took our positions.

I could see by the way her tits moved around that she was not wearing any bra under that flowery dress.   Convinced that my dynamite serves would soon have her stripped down naked I grinned like the cat that got the cream.

Perhaps because I had not picked up a bat for about forty years I was not quite as dexterous as I thought I was. Soon I was dancing around in my bare feet having had to surrender my shoes and socks, while Deborah was only missing one shoe and by the time she had to remove the other I was down to my underpants.  She continued to play like a champion and the next ball that shot past my left ear meant that I had to take them off.

My opponent stood at the end of the table with a big smile, as red faced I slipped my shorts down and quickly covered up my crown jewels with my hands.

“If it will make you more comfortable,” she said, I’ll take my clothes off too – then we’ll be equal.”

I nodded my head furiously in agreement and she proceeded to pull the dress over her head and slip out of her panties. Holy shit I almost came there and then, she had an incredible body and she made no attempt to cover it up.

“Now,” she said, walking up to me and poking me in the chest, “as you lost you can give me a massage.” With this, she went over and lay face down on the padded table.

It had a hole that she put her face through and I, with a completely ulterior motive in mind, decided to stand at the front of the table and knead her shoulders. This meant my enormous boner was hovering in front of her face and has I leaned forward to reach further down her back it came into range and she licked it. I was not close enough for her to engorge into her mouth but she did take the head between her lips.

She obviously knew that I wanted her to suck it and she quickly got up and told me to sit on the table, I did as she bid with my legs hanging over the side. She spread her legs, leaned forward with a hand either side of me, took my dick into her mouth and started to do pushups. I wanted to cum the first time it slid between those luscious full lips of hers but she made me wait as she slowly lowered herself, raised up again and then pausing for a split second she plunged back down on my throbbing cock.

Having a problem to stand the suspense I grabbed hold of her head and tried to face fuck her but she broke my grasp and continued her tortuous moves until my balls felt they were going to explode.  When I did cum it seared through my pipe like red hot lava and into her pretty mouth.

As soon as she’d drained my balls I jumped off of the table, and we changed places. I shoved her legs into the air and a put my face between her warm smooth thighs and started to nibble at her pink folds.

“Lick it for me, ” she cried, “lick it.”

I responded by lapping her cunt up and down like a big puppy dog.

“Fucking hell!” she yelled as I went faster and faster, “I’m going to cum.”

She wrapped her legs around my neck and almost suffocated me as she went into a massive orgasm. As soon as she’d regain her senses she slipped off the table turned with her beautiful ass towards me and invited me to stick it into her twat. It felt so hot and wet inside and I took a deep breath, grabbed onto her tits and I drove it in and out as she kept yelling “ veloce,  veloce.” Meaning she wanted it faster.

I moved my hands from her tits grabbed onto the table for better traction and then I fucked her like a madman. When I came we both yelled out loud and she shoved her ass back against me as hard as she could.

“WOW, that was good,” she said, turning around to kiss me, “Where have you been all my life?”

As crazy as it seems we spent the night together on the Pool Table using the felt dust cover as a blanket. We fucked a couple of times during the night and once before I left in the morning.

I hated to say “Arrivederci!” but I had to go before someone discovered my car and got curious. However, I did promise to look her up in Milan sometime.

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The characters portrayed in these stories are fictional and any similarity with persons living or dead is purely a product of your own imagination.

Copyright Cristiano Caffieri 2017. You may not sell, license, sub-license, rent, transfer or distribute any part of these stories or the photographs herein in any format, or claim ownership.

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