A Bareback Rider – Pt 09 – Dorothy and Barbara

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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

Dorothy was the first steady girlfriend I had in Dublin, she worked as a waitress in her mother’s café, which was one of those egg, chips and beans kind of places. Once I’d taken her out a couple of times I got my meals for free, although I always offered to pay. Even when I tried to leave a tip it was slid back into my pocket.

She was another of those naïve Irish girls, or should I say, just solidly against sex before marriage. Unlike the average colleen, she was not Catholic, she was one of those rarer Church of Ireland Protestants, but she was obviously still influenced by the Pope.

When the restaurant closed and the family moved upstairs to their apartment we’d sit at the fireplace in the corner of the restaurant and neck. She was a great kisser but if my hand strayed an inch from her waist I got my knuckles rapped. It was very frustrating. Of all the celibate women I looked back on she was the one I felt would not succumb to my lifetime of experience and new found charm, however, I thought I’d give it a try.

Perhaps it was because I’d accepted the possibly of defeat before I’d even started the process, that caused me make an error in my calculations. When I materialized in Dublin, I found to my horror that my timing was off by four years.

It was when I entered the café that was so familiar to me, that I realized my mistake. As I squeezed my way between the tables I immediately caught sight of Dorothy eating lunch with her kid sister. When we broke up, Barbara was just a 14 with braids, now she was a well developed 18 year old with boobs, quite big ones in fact.

They invited me to sit with them and ex my girlfriend, who’d also blossomed nicely, couldn’t wait to wave a diamond ring in my face.

“Look I’m engaged,” she laughed, “how’s your life?”

Of course, she would have fainted if I’d have told her that I was back from the future so I just said that I was passing by and thought I’d say hello.

“You must have passed by here a lot of times during the last four years,” she teased, “what’s wrong – did you suddenly find yourself in need of female companionship.”

“The little bitch is physic,” I thought to myself, but then I laughed it off and said that I would be prepared to take her dancing for old times’ sake if her fiancé had no objection.

“I’m afraid Liam is very possessive,” she smirked, “and much more of a gentleman than you ever were,” I presumed she was referring to the fact that I’d dumped her because the relationship was going nowhere, but I remained silent.

It looked as though my transition through time and space had been a waste of effort until Barbara spoke up. “I’ll go with you,” she said.

Dorothy looked positively uncomfortable, and even more so when I said OK and arranged to meet her at the National Ballroom at 7.30. After spending the rest of the day wandering around some of my old haunts, I ate supper and then returned to my little apartment. I had a quick wash and shave, and put on my gray gabardine double-breasted suit and a pair of gray suede shoes. In the streets of 2017 I would only have attracted ridicule but in 1957 I was the sharpest dude on the block.

I must say Barbara looked very nice, she wore a full skirt that reached just below the knee, a white blouse and brown shoes with a Cuban heel. Her long fair hair was in a ponytail and she had just a hint of make-up.

I’m not sure what my intentions were at that moment, I’d traveled in time intending to seduce her sister but here I was with a very pretty young girl preparing to slow dance the night away. Cheek to cheek we shuffled around the floor and I ventured at one point to place my hand on her bum. She didn’t object and that was a good sign, but one the men hired by the management to ensure moral conduct was observed, did give me a warning.

Around 10.30 I suggested we should go back to my place and have coffee. It was drizzling rain when we got outside, I took off my jacket and draped it around her shoulder and hailed a cab. A few minutes later we were picking our way through the boxes that littered the first floor and made our way to the stairs that led to my lair.

I told her to make herself comfortable while I slipped back down to fill the percolator, then I put it on the gas ring I had in the room and turned my attention to my very pretty guest.

“Have you got any Gin,” she asked, lounging back on my bed.

“I have brandy,” I said.

“That will do.”

I went to my cupboard, that doubled as my cocktail cabinet and poured us both a glass. Barbara didn’t sip it in the customary way but knocked it back in a single gulp.

“That’s not bad,” she commented after coughing for a while, “top me up.”

I was feeling a little uncomfortable plying her with drinks but I could hardly be inhospitable. However, by the time the coffee was done she’d had four, and I was hoping she wouldn’t ask for more.

When I handed her a mug she sipped on the coffee looking at me thoughtfully.

“Did you fuck my sister when you went out with her?” she asked.

I almost spit out my coffee, I was shocked, very few women I knew in Dublin at that time used language like that.

“Your sister and I did not cross that line,” I stammered, struggling for something to say.

“Well you lucked out because she’s fucking Liam, I came across them one day with his bare ass going up and down like a fiddler’s elbow.”

I must admit that there was a little twinge of jealousy even after all those years but Barbara soon took my mind off of that.

“I’d much rather fuck you than Liam,” she said, getting up from her seat and fingering the front of my shirt. I was a little nervous because of the alcohol she’d consumed. I didn’t want to be accused of taking advantage of a drunken woman. However, she seemed quite steady on her feet and undid my buttons one by one and then slid her warm hands inside my shirt and rubbed them up and down my chest.

My groin, which had been hotting up for some time, had now reached boiling point and I grabbed her shoulders and crushed my lips against hers. She dug her nails into my bare flesh as the kissing became more and more intense and I slowly moved her back toward the bed and guided her body downwards.

Continuing to touch her lips lightly with mine I unbuttoned her blouse and then raised her back so that I could get her bra out of the way. When her tits popped out I took a deep breath and then lowered myself down and began to suck and her erect nipples. As Barbara groaned and moaned she flung her arms across the bed and I moved back a little, proceeded to remove her skirt and then her panties.

She lay there naked on the bed squirming impatiently as I took off my clothes, and when I stood there with my cock standing hard and upright she put her dainty bare feet in my groin and played with my cock and balls. I just closed my eyes and leaned back and enjoyed it for a while and then she leaped off the bed like a wild cat, knelt down before me and plunged my dick down her throat. Delicately kneaded my nutsack with both her hands she slid it in and out of her mouth. My whole body seemed as if it were on fire and I wanted to cum so bad I was tempted to grab onto her head and face fuck her. There was no need for that however because I suddenly felt my sperm searing up my dick like hot lead and into her mouth.

Barbara milked out every last drop and when I withdrew it from those sweet lips I took her under the arms and literally flung her on the bed. Burying my face between her thighs I parted her pink folds with the tips of my fingers and I lapped my tongue across her warm moist crack. She cried out, “Holy Fuck,” as I proceeded to lick her cunt as if it was the flavor of the month.

As I continued to swipe my pussy fluffer up and down her hairy crevice she gripped onto my head and started to mumble incoherently. I could now feel a slight trembling and I knew she was getting close to orgasm. When she did cum her ass began moving up and down and her quivering body must have registered nine on the Richter scale.

Holy shit she flung her arms and her legs all over the place and I eventually pinned her down and drove my cock into her. At the moment she froze, took a deep breath and then relaxed as I began to slide it in and out slowly at first and then more rapidly as I had the urge to cum.

I figured she’d scream when I shot my load and I was right, and as I made those final thrusts, crashing against her pussy with considerable force, she wrapped her legs around me and held me there. Before the cum had stopped dripping out the end of my dick there was a loud knocking on the door downstairs. At that time of night, I knew it could only be one person and I didn’t even bother to put on my clothes.

When I opened the door it was her, Dorothy. She shook her head as she looked me up and down.

“Where’s my sister?” she yelled, charging past me and making for the stairs.

I followed her closely up the steps and into the room. Barbara still lay there naked,

“Guess what?” she said, addressing her sister, “I’ve just had the best fuck of my life, why don’t you join us for a threesome.”

Dorothy turned and looked at me with pure venom in her eyes, “Did you get her drunk?”

Our faces were very close to each other as I told her I didn’t have to, Barbara wasn’t a prude like her. She was just about to slap me when I grabbed her hand, pulled her towards me and kissed her. She struggled free, “What are you doing !?”

“Loosen up,” cried Barbara, laughing and sticking her legs up in the air like a giant wishbone, “loosen up – I did and it was wonderful!”

“Dorothy shook her head and turning back to me she simply said, “You bastard,” and she strung her arms around my neck and crushed her lips against mine.

That night I fucked and I sucked until I was completely exhausted. Those two women had a good deal of sexual tension pent up inside and they seemingly released it all in one session.

Researching online I recently discovered that Dorothy and Liam did marry and actually celebrated their 60th anniversary, and although she would not be able to remember our encounter, I wonder if she ever thinks about the six months we were an item and regrets not loosening up a little bit. THE END

Sex Toys – Great Photos

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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