Penny - How It Started Ch. 01

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Penny overcomes her embarrassment.
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Part 1 of the 2 part series

Updated 06/09/2023
Created 08/08/2019
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Penny found the train journey across Europe quite romantic. Not in a hearts and love sense but more of a rose-tinted view of travelling. Her studies were behind her and she was lucky enough to be able to take a little time out to travel before starting work. Not a gap year – she wasn't that lucky – but she did have the summer off to enjoy and relax the transition between study and work.

Her friend Jenny was with her, along with one of Jenny's friends, Sue. Jenny and Sue had that easy confidence with everything they did – and also with their bodies. Penny was always a bit embarrassed when the other two would change their clothes or dry off after a shower in front of her but they just seemed oblivious to their bodies.

A little too oblivious for Penny. Jenny always seemed to be touching Sue's leg or her back and when they were changing Jenny always found a reason to help Sue's breasts into a bra or a top. Once, Penny walked in on them and they both had their short skirts hoisted above their waists, white panties at mid-thigh level and fingers stroking their pussies. Penny was mortified but Jenny just said that it was perfectly normal and why didn't she join them.

Penny made up some excuse and left, red faced and sweating – but she did stuff her own hand down her panties when she got to her room and brought herself to orgasm in record time.

After that, Jenny seemed to find any excuse to bring up sex – and specifically masturbation – with Penny. "Do you masturbate, Penny? You must do – everyone does. How often?" or "Doesn't that lead singer look sexy? I'll be fingering myself while I look at his video later – won't you?" But Penny just mumbled something vague and looked away.

So really, what happened on the train was no surprise at all.

Jenny had been flirting all day with a much older man called Peter and now all four of them – Jenny, Peter, Sue and Penny – were in the buffet car. The barman had closed up and brought down the shutters and Jenny was leaning forward on the bar, peering at the menu. She was wearing a very short skirt, flesh coloured tights and grey, knee length, high heeled boots. As she leaned forward, the skirt rode up and showed a large expanse of nylon clad thigh, the bottom of her bum cheeks and a hint of her white panties.

Peter had been looking at her legs in the boots and suddenly got up and stood next to her and put his arm around her waist. Getting no reaction, he stood behind her and started running his hand over her skirt-covered bottom. Again, Jenny didn't react, just kept peering at the menu and even thrust her bum a little more towards Peter.

Jenny continued peering at the menu while she softly hummed a tune to herself, as if she didn't even know that Peter was stroking every inch of her inner thighs, her bottom and even occasionally the front of her panties.

"Come on – I've got to see this!" said Sue, grabbing my hand and dragging me next to them. Sue was openly rubbing the front of her panties as she watched Peter lovingly fondling Jenny's bottom. "Oh, go on!" she said to me, "Enjoy yourself while you watch."

I was very turned on but I was too nervous to play with myself openly like that. Even if Peter had now released his penis and was blatantly rubbing it against Jenny's skirt, sometimes lifting it to rub it against her panties. Suddenly, I noticed Jenny smiling at me.

"Peter – don't you think Penny has lovely big breasts?" she said to him. "Do you like big breasts? Have you ever felt any as large as Penny's?" And then, turning to me, she said the fateful words "Penny, let Peter have a feel of your breasts."

With that, two things happened. Jenny opened her thighs to let Peter's cock slip between them, the top of his shaft now deliciously rubbing the underside of her panties and effectively masturbating her as well as him. And Peter reached out a hand and very gently started squeezing one of my breasts.

I couldn't move – I was paralysed. I wanted to run but at the same time I was enjoying his hands on my breast so much, his finger occasionally rubbing across my nipple. Now I did want to play with myself but my upbringing still held sway and wouldn't let me.

Then I noticed the lightest of touches on my thighs, slowly sliding up to my panties – and under them. Sue's fingers had found my very wet pussy. She played with me with one hand and with herself with the other, as Peter continued grinding into Jenny and was now delivering a full-on grope of my breast, having eased it out of the safety of my bra.

Glancing down and seeing three short skirts raised up, Sue playing with her own pussy, mine played with by Sue's trembling fingers and Jenny's displaying her by now soaking panties being prodded by his own penis was just too much for him and with a long moan he shot load after load onto Jenny's panties and skirt.

Sue was still frantically frigging herself and me and Jenny pushed Peter to one side, stuffed a hand down her own panties and started rubbing her clit as her lips met mine and she gave me the softest of kisses and little flicks with her tongue.

Sue had already started building to her orgasm and I couldn't last any more. I had the most intense orgasm of my young life, right there in the deserted buffet car, while my two friends kissed and frigged me.

Later, in my bunk, as I played with myself this time, I realised that the embarrassment actually helped make the orgasm more intense. I could live with embarrassment if it made sex this intense.

Which was just as well, because Jenny had many more plans for me and for my sexual education.

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