A Bareback Rider – Pt 01 – Janet

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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

Having assumed my powers as a time traveler and shapeshifter today I have chosen to go back to the first job I ever had. It was working for a small greetings card company in the UK. Although it employed mostly women and seemed an ideal job for a horny teenager – it was actually very frustrating. The truth is – I had a problem, I looked more like fifteen and despite all my efforts to look and act older nobody wanted to date a fresh-faced kid with a weird Italian name.

There were several girls there my age but they were dating more mature types. They teased me and even flirted with me but when I asked them out they tended to laugh in my face.

Janet, the bosses secretary, who looked like an attractive librarian, with horned rimmed glasses and hair done up on top, was different. She seemed sympathetic and although I didn’t realize it at the time I think she was coming on to me. In fact, she once said, “Have you ever thought of asking someone a bit older?”

Now she was around 25 and it never entered my head that she would be interested in me until about twenty years later.  Today I’m going to travel back to 1951 and stand by her desk on the very day she spoke those encouraging words.

“Have you ever thought of asking someone a bit older,” she said after Pat from the accounts had just teased me about my boyish appearance.

I waited until Jean had left and then I turned to Janet, “I don’t suppose you’d be interested?”

She gave a faint smile, “Are you asking me out?”

“Why not?” I said, rather amused that she didn’t realize that my youthful façade concealed a man who had more sex that she’d had hot dinners.

“I don’t think your parents would approve,” she laughed, pretending to straighten some files on her desk.

“I’m not going to tell them, why should I?”

She looked at me coyly, “Where do you plan to take me?”

“What about a movie?”

She paused, I could tell that she was nervous about going through with it but after a few shrugs and a sigh, she said yes. In those days most of us didn’t own cars and so I arranged to meet her outside of the Regal on the following Saturday. When she turned up she was dressed a little bit more fashionable than usual and was wearing a sweater that accented her perky tits. She also wore makeup that I’d not seen her do before. All in all, the somewhat sedate secretary looked very attractive, quite sexy in fact.

After a friendly greeting, I took her by the hand and led the way into the movie house. I could see she wasn’t quite comfortable with that so I let go thinking that in the darkness of the cinema I might be able to hold more than her hand.

I’d made sure that my time traveling was well financed and so I paid for the best seats. The usherette who showed us to them gave me a furtive glance, perhaps wondering if I’d brought my teacher along.

My plan was to take it easy during the B-movie and to refrain from putting my arm around her until the big picture.  You must realize that back in those days people were much more reserved and I didn’t want to scare her off because some girls at that time would just get up and leave if your behavior made them feel uncomfortable.

As the RKO logo flashed on the scene for the big even I slowly slipped my arm around her shoulder, she glanced sideways at me, as if to say, what the fuck are you doing, but she didn’t pull away. Halfway through the movie, during a romantic scene, I drew her closer to me until her cheek was against mine. Surprisingly she seemed to like that and snuggled closer – the ice was broken.

After the show when I mentioned going to a restaurant she seemed a little reticent. I think she was afraid of being seen by her friends and she suggested we could go to her place and she’d rustle up something.

She had a bachelor pad in an old converted house and we had to take a bus to get there. Once again, when I attempted to hold her hand she pulled away. It didn’t look very promising.

We quietly entered the hallway of the old house that had been turned into four apartments and after looking around furtively she quickly turned the key and hustled me in.

“We have to be quiet,” she whispered, “The neighbors are very nosey.”

Her place was just one big room, it was decorated in Canary yellow and the cushions on the big chintz-covered sofa were the same color. It seemed that this piece of furniture also served as the bed.  There was a little kitchen unit in the corner above which was a shelf with a number of jars with yellow lids and there was even a yellow throw rug on the floor. Considering this was just 6 years after World War 2, with lots of things still in short supply, she’d done a nice job making her apartment attractive.

“What would you like to eat?” she asked, “I could make you a ham sandwich.”

Bearing in mind that nobody had freezers of microwaves back then, there wasn’t much more a person could put together at short notice. I said that would be OK and then I sat and watched her putting on the kettle and making up the sandwiches. She had a lovely ass and very shapely legs and I was wondering what my chances were of seeing her naked before the night was out.

We sat at a small table in the corner of the room to nibble our sandwiches and sip on our tea. She kept glancing at me every so often and made several attempts to make idle conversation but I somehow felt that she was probably imagining what it would be like to fuck me.

As soon as we’d finished we sat on the sofa together and as few people owned a TV back then, she turned on some soft music. I leaned over switched on the table lamp next to me and then got up and switched off the main light. When I turned around to walk back toward her she looked terrified.

“What are you doing?” she asked, swallowing hard.

“I just wanted it to be a bit more romantic,” I replied, sitting down beside her.

“We are just two friends spending the evening together,” she protested, “Nothing more.”

Just like in a movie I leaned forward and removed her glasses and placed then on the side table.

“What do you think you’re doing,” she asked once more, moving her face away from mine.

I didn’t give her a chance to say anything else, I grabbed her shoulders, brought her up close and kissed her. It felt as she was going to break my grasp at first but then she surrendered and we ended up in a passionate embrace.

With my lips still crushed against hers, I ran my hand underneath her top, very quickly forced it under her bra and felt her firm warm tit in the palm of my hand. She struggled to break my grasp, “I think you’d better go home she gasped, this has gone too far.”

“What did you intend to do when you invited me to your apartment?” I asked,  “just sit around and play cards or something.”

At first, she seemed lost for words and then she blurted out that I was too young to make love to her, “It’s just not right.”

I said that she should let me be the judge of that and I crushed my lips against hers again. This time she responded enthusiastically and when she popped her tongue into my mouth I knew it was all systems go.  I put my hand up the back of her top, unhooked her bra and then I laid her down, unbuttoned it and began to suck on those loved firm tits.

Her body began to shake all over and when my hand slipped up her skirt and my finger found its way around her panties and into her wet crack she just let out a loud moan. Soon I was helping her out of her clothes and then I stood up and stripped off.

I must admit I had a puny body at that age but I did have a big dick and as she lay there on the sofa I stood by the side of her face and touched her lips with it. She nervously gave it a little kiss and as I pressed it against her mouth she opened up, closed her eyes and began to work up and down my shaft.  It felt great and even better when she started to run her slender fingers around my balls.

When I felt my cum moving up my pipe I intended to warn her but instead of saying I’m cumming, giving her a chance to withdraw and finish it off with her hand, I said, “I’m cumming in your mouth.” And that’s what I did. She didn’t resist, she simply swallowed it and lay there with her eyes closed as if she was too ashamed to look at me.

Taking her by the feet I repositioned her so that I could place my face between her thighs. She was twitching a little as if anticipating my next move. I knelt before her, gently separated her long slender legs and worked my way up to her hairy muff. When my tongue flicked across the lips her body stiffened up and she reached down to grab onto my shoulders.  I used my fingers to probe her pink petals and then I licked all the way from her anus to her clit. She went ballistic.

Janet had sucked me good and I intended to give her the best tongue lashing she’d ever had.  As my pussy fluffer worked up and down her crack and my hands reached up to tweak her nipples she moaned and groaned and squirmed her ass around as if she was enjoying every second of it. It was a far cry from the reluctant woman of a few minutes earlier.

When I felt her vulva begin to tremble I knew she was about to cum and I pulled out all the stops to give her the best orgasm possible. When she’d finished shaking I positioned myself above her and the drove my dick deep inside of her. She gasped and dug her nails into the cheeks of my ass as I began to ram it in with considerable force. It wasn’t long before my balls went on the boil and I shot my load inside of her. She almost cried and dug her nails deeper into my ass as I gave those last powerful thrusts.

The two of us just lay there for a while and we didn’t say anything. It was Janet who spoke first, “Where did you learn to make love like that?” she asked.

“From a book,” I replied, kissing her pussy mound before getting up.

“That must have been some book,” she smiled.

“It was,” I said, “I wrote it.”

Janet was still worried about us having a relationship and suggested that we could meet at her apartment occasionally but she didn’t want anyone to know at the office to know and suggested that we just act normally towards each other.  That was great news, it meant I could drift in and out of that time period whenever I choose. END OF PART ONE – STAY TUNED

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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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