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Paula And The Unexpected Encounter

"Paula meets a new friend who also likes to cross-dress"

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After I graduated from University, I stayed in the same town because I had been lucky enough to find work in the field I had studied while at Uni.

I realized that it would be a whole new life for me as I would only see Dee if I went home and Maggie no longer lived in the town, so I only saw her when she came home to see her parents. On the plus side, I now had a small flat of my own so could be dressed when I was at home. Oh, the pleasure of getting home after work and being able to put on some soft silky undies and feel of material caressing my body even as I stroked it into place. We dressed casually at work and I felt safe enough to wear stockings, a garter belt, and panties under my trousers, so, in a way Paula was always with me.

On Fridays, after work, a group of us would congregate in a local bar to have a social drink to start the week-end. Over a period of time, I noticed a good-looking, almost pretty, guy who I guessed was the same age as me and also was a regular Friday night socializer. I got the feeling he had noticed me for some reason so I was not surprised when we happened to be alone in the gents washing our hands when he said, "Seamed or plain." I pretended not to understand but he grasped my hand and pressed it against his trousers and I could feel the clip of a suspender strap and realized he was wearing stockings.

"Mine are seamed," he said. Then he pressed his fingers against my suspender clip.

"Mine are plain," I confessed.

"Would you like to see mine?" he asked.

"Yes, please," I quietly replied.

"My apartment is just down the road," he said. "We could get a pizza on the way."

He introduced himself as Henry but added that he used the name Helen when dressed, I told him my intimate friends called me Paula and I hoped he would do the same. We collected a pizza and during the walk to his apartment, I told Helen how Paula had come into my life. Once through her front door, Helen took off her jacket then her shoes and socks. I could see her stockinged feet. I followed suit and we undid and dropped our trousers at the same moment. Helen revealed a red six-tab garter belt, sheer black seamed stockings and, red satin panties. Like Helen, I was wearing a six-tab garter, sheer stockings and, pale blue French knickers.

"I love your knickers," Helen said, "Such a turn-on."

I was equally turned on by the vision that Helen presented, even more so once she undid her ponytail and let her hair fall naturally, she looked really beautiful.

"I'm going to put on my favorite dress and lend you a bra and slip."

She put on a red satin bra and then a white cotton dress that had a simple flower pattern on it. She looked stunning. Once in the borrowed bra and slip we went into her sitting room to have the pizza together with a glass of wine.

"So, how did you get started?" I asked.

This is Helen's story.

-

It was my Aunt Jane who led me astray. She is my mum's youngest sister and I always liked her as she seemed to understand me. Mum and Dad were invited to go on a summer break with some friends, so Aunt Jane was asked to look after me while they were away. I arrived at Jane's on a Sunday evening and woke up on Monday morning to hear the washing machine going. It was hot even that early in the morning so shorts, tee shirt, and sandals were more than enough. I joined my aunt for breakfast.

After breakfast, she unloaded the washing machine and asked me if I would be a good boy and hang out the washing on the line, to which I agreed. It was only when I began to hang out the washing that I realized it was all her intimates.

Suddenly as a randy teenager, I was fondling women's stockings, bras, and panties, just holding these things was enough to get me excited and I hoped no one saw me sort my shorts out to hide my otherwise obvious erection. I did not know it at the time but Jane later told me she had watched the whole time and it had excited her. When I came back into the house, using the wash basket to hide my stiffness, Jane said she needed to do some shopping, so into town, we went.

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I was vaguely aware that she seemed to be buying lots of lady's undies but was quite happy to go into shops with her that I normally would never dare enter even though I was attracted to what they offered. When we got home Jane asked me to collect the washing and bring it up to her bedroom. Of course, doing this had the same effect on me as earlier and again Jane watched me as I sorted my erection, that was not hidden by my shorts, while fondling the slips and knickers that I put in the wash basket. Up in Jane's bedroom, she asked me to help put the items away.

Having done this. she said, "Your mum tells me that I am your favorite Aunt, is that true?" to which I replied, "Yes."

"So, you will do whatever I ask you to do?"

"Of course," I said.

"Then go into your bedroom and put on what I have laid out on your bed and then come back and show me," she said.

I went into my room and saw lying on the bed, a garter belt, stockings, panties, bra, and a sheer silk slip. I was surprised and at the same time secretly pleased and excited. The morning's shopping had been for me, not my Aunt as I had assumed. Don't take all day she called as I began to change. I understood enough to clip garters to the stocking and then pull on the very silky panties that had me hard even as I pulled them up my legs. The bra and slip followed but the bulge from my stiffness would not go down, I was too excited, and it was very obvious.

I wondered if Jane would be shocked but then realized that she had asked me to get dressed, so she clearly knew what she would see.

I made my way into her room. She, too, had changed for she was sitting on the end of her bed wearing stockings, sheer panties, a peephole bra, a micro mini skirt, and a sheer blouse that hid nothing and certainly not her nipples poking through the peepholes in her bra.

"Henry, you look beautiful," she said, "but we can't call you Henry when you are dressed, can we, so how would you like to be called?"

I thought a moment and then decided on Helen as my name because Helen of Troy was a legendary beauty.

"Come closer, Helen," said Aunt Jane, and I did as requested. She stroked the front of my slip, which made me tingle and almost cum in my panties.

"Do you like what you can see?" she asked as she stroked my stocking-clad legs. I nodded my agreement.

"We need to sort your hair." As she said this, she turned me to face a full-length mirror and then stood behind me as she combed my hair into a central parting with soft bangs framing my face. Much to my pleasure, I now saw a very pretty gurl staring back at me with Aunt Jane standing behind her. Jane hugged me to her and at the same time slid a hand under the hem of my slip that then grasped my rigid boy clit through the silk of my panties. That was all that was needed as I lost control and thoroughly soaked my knickers and slip with my cum.

"Goodness," said Jane, "now there will be some washing to put out in the morning. Go and change, and then we will have a fun girly day together."

-

It was quite late by the time Helen had finished her story. We were sitting side by side on her large sofa and it was obvious, from the state of our knickers, that we were both very excited by her memory. I gently lent towards her and as I softly kissed her my hand slid under the hem of her dress and grasped her rampant boy clit shielded only by the damp patch at the front of her silky panties. Helen returned the compliment grasping my equally hard boy clit with the result that we both came together.

Afterwards, I accepted Helen's invitation to stay over. So began a very exciting and enjoyable week-end but that is a story for another time.

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Written by 2Bkilnhill45
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