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Paula's Progress

"Paul's further experiences with his sister's help since 'Becoming Paula'"

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Having agreed with sister Sue to enter the town's fancy dress competition as Cinderella and Prince Charming, with me as Cinderella and her as the Prince, I had discovered my liking for wearing girl's clothes. The feel of them, especially the undies, turned me on so much that I became stiff even as I started dressing. Sue's answer to this problem was that I would have to wear knickers all the time till I got used to them and also be fully dressed at the weekends.

So there I was on a Saturday morning in her bedroom preparing for the day. At that moment, I was just wearing a tight waspi as a way to give me more of a figure and was clipping on the sheer black stockings, that Sue said made my legs look more shapely, prior to stepping into a pair of silky French knickers. Too often in the past, they had been my downfall because they felt so sexy and made me stiff.

At that moment, Sue came in carrying two packets with the comment "For us" as she began to unpack them. I was busy arranging my bra prior to padding it out when Sue said "For you" and handed me a couple of breast forms. I was surprised and then delighted and once they were in place, I was so busy looking at myself in the mirror to gauge the effect that I hadn't noticed what Sue had got for herself.

It was only when she said, "You look good enough to fuck," that I turned to look at her and saw a distinct stiffness hidden by her 'Y' fronts.

"What on earth ...?" I exclaimed.

Sue slipped her 'Y' fronts down and revealed the strap-on that she was wearing. "You know," she said as she pulled her briefs back up, "I almost know what it must feel like to be a bloke."

"I can see that," I said as I stood beside her and then grasped her cock through her underpants. I gave it a few firm pulls that resulted in a brief sigh and a tensing of her thighs to show me that my fondling had had the desired effect on my tom-boy sister.

"Stop that and finish dressing," she said. "I'll get some coffee and then we can have some real fun." I knew exactly what that meant from the way that Sue's nipples made stiff little points in her tee-shirt, showing that she was very excited.

I was barely conscious of the front door being answered as I put on a simple dark blue cotton dress that buttoned all the way down the front and showed off my figure to its best now that I had properly shaped breasts that jutted forward proudly.

I had just finished arranging my hair into a page boy style when Sue came into the room followed by Phoebe who, from the way she was dressed all in white with a very short pleated skirt, looked as if she had been playing tennis, however, I was surprised that Phoebe didn't immediately recognise me even though Sue had introduced me as her friend Paula.

She sat on Sue's bed and I sat next to her while Sue relaxed in the chair opposite. I reflected that I hadn't seen her since the time of my initiation into wearing lingerie and I had certainly come a long way since then. So we sipped our coffees as Sue and Phoebe chatted about boys. Noticing my quietness, Phoebe asked me if I knew Sue's brother Paul. Taking my cue from Sue, I shook my head. What Phoebe said next surprised me even more. "You should," she said, "I won't say how I know but he's got the most beautiful cock."

"He has?" I said, somewhat stunned.

"Oh yes," she said, "and it's really quite big."

"Really?"

"Yes, really."

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At that moment, a naughty thought came into my head.

"Is it as big as Sue's?" I asked.

Now it was Phoebe's turn to be baffled.

"Sue's?" she said looking at my sister.

"Yes. Why don't you show her, Sue?" I said and, true to her nature, Sue got up from her chair and stood in front of Phoebe with her legs slightly apart, then pulled her shirt out of the way. With hands on hips, she thrust her pelvis forward so the outline of her erection could be clearly seen under her shorts.

"Oh!" said Phoebe.

"Go on, have a proper look" I urged and Phoebe, with nervous hands, began to undo Sue's shorts and pull them down to reveal the erection hidden in Sue's 'Y' fronts. "Go on," I repeated and Phoebe pulled down the cotton briefs and was faced with Sue's upright cock.

"Don't stop, play with it," whispered Sue, so Phoebe did just that and I could clearly see the effect it had on the both of them. The way that Phoebe was wriggling around on the edge of the bed led me to put my hand on her thigh and slide it up under her short skirt. The fact that she let her legs fall apart as I did so only encouraged me and soon I was stroking the damp front of her satin panties and as I stroked her mound it became even damper.

"Suck it," said Sue and I watched as Phoebe's mouth took in the erection before her. As she did this, I probed under the elastic of her leg hole and soon my fingers were stroking her and teasing her clit. She stopped sucking briefly to say she wished it was a real one.

"Paula's is," said Sue.

I think at this point, Phoebe had ceased to be surprised by anything we said and she simply looked at me with a new realisation and then watched as I undid the buttons of my dress and she could see the obvious projection tenting my black silk slip. I led her hand under the hem and onto the erection barely contained by my French knickers. She pulled my rampant prick out of a leg hole of my knickers and then bent down to kiss and suck the bulbous head of my hot cock. As she did this, I slipped my hands inside her blouse and grasped her breasts. I could feel her nipples hard against the palms of my hands through the thin fabric of her bra. I gently squeezed them and she responded by sucking me more enthusiastically. At the same time, Sue climbed on the bed behind her and, lifting Phoebe's skirt out of the way she pulled her satin panties halfway down her thighs before sliding her strap-on into Phoebe's hot and eager cunt.

Phoebe's reaction was to suck my cock even more enthusiastically so I lent back and let her enjoy herself. I don't know who came first. All I remember is that in the heightened atmosphere we seemed to reach a mutually satisfying climax in a very short time and with mutual sighs collapsed on Sue's bed in happy release.

"The things you two get me doing," said Phoebe with a smile as she began to stroke me through my silky slip that only got me aroused again as we prepared for another bout.

A few weeks later, Sue and I won the fancy dress competition even though some of the judges weren't sure if the prise had gone to two girls, two boys or what. Anyway, there was a nice young photographer there called David who seemed much taken with me and asked if I would pose for him as Cinderella at his dad's studio the following weekend.

I agreed to this and so began another stage in my education.

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Written by 2Bkilnhill45
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