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Paula Hears Dee's Tale

"Dee tells Paula how she became a cross dresser"

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It was a week later when I returned to the studio, and I was looking forward to seeing Dee again now that we both knew that we both liked wearing girls' clothes.

"I wasn't sure you would come," she said as she let me in.

"Not come?" I was surprised. "I expect to come here often, and in all meanings of the word, especially when you look as stunning as you do now," I replied.

Dee was wearing a simple cotton dress that had a translucent quality, and when she stood by the window with the light shining through it her slender figure was silhouetted against the material and I could make out the sexy lingerie she was wearing underneath; the image turned me on so much that I decided to be as provocative as possible during the planned photo session.

Instead of using the changing room, I began by changing in the studio, knowing that Dee would be watching as she prepared the camera.

I stripped off my outer clothes to reveal that I was already partly dressed, for I was wearing some sheer black silk panties, a black satin garter belt holding up sheer black stockings, a simple bra, and a black silk camisole. The silk of the camisole had me excited already and I do love the feel of tightly clipped stockings making my legs feel nice and smooth. I sorted my hair and put on some light makeup. By the time I was ready, I could see that Dee too was excited, if the bulge in her dress was anything to go by, and knowing that I was partly responsible for that gave me a great deal of pleasure.

"Well now," I said, "how about telling me how you got started as we work."

"Alright," said Dee.

So this is Dee's story:

It began as an intended practical joke. I was at college at the time doing a photography course. Some classmates said that a girl that I liked wanted to meet me at a local pub the following Wednesday at eight o'clock, so I went. What I didn't know was that on Wednesdays this pub was a meeting place for TV's and transsexuals.

Anyway, I arrived on time, got myself a drink, and then sat down away from the bar. I was vaguely aware of a group of girls drinking nearby in a more private part of the bar. One of the girls walked past a couple of times on the way to the bar and she obviously realised that I was waiting for someone. I must have been there for half an hour or more when this girl, Annie as she told me later, stopped and asked if I was waiting for someone. I said yes and Annie said why not join them while I waited. So I did.

I noticed that one or two of the girls seemed rather masculine but I was enjoying talking with Annie so much that I didn't make anything of it. At the end of the evening, I gave Annie a lift home and although she invited me in I said no, but we fixed a date to see a film the following Friday.

When she invited me in for coffee after the film I said yes, little realising what it would lead to.

After she put on the coffee she said she was popping upstairs to fix her makeup, so I sat on the couch in her sitting room and idly looked at the magazines on the nearby table. I notices that a couple of them were aimed at transvestites and she-males. I picked one up and in no time I was both intrigued and turned on. At this moment Annie returned.

"Oh," she said, "I didn't mean to leave those out."

"It's cool," I replied.

"Do you like them?" she asked.

Well, I hummed and aah'd but admitted that I found them quite exciting,

"So I see," she said, for she had noticed the bulge in my trousers even as she sat down beside me. "I'm so glad you do," she added and gave me a big kiss, to which I responded enthusiastically.

I think at that moment I realised the truth about myself and guessed the truth about Annie.

Anyway, we started to get more passionate and as she stroked my leg I unbuttoned her blouse and began to fondle her firm tits through the thin silk of her bra. It had a front clip and she made no protest as I undid it, her only response was to slide her hand further up my leg and over the front of my trousers where she could obviously feel my stiff and upright penis. I began to kiss and suck her nipples and in return, she unzipped my fly and slid her hand into my briefs and onto my cock.

We were getting very worked up by this time as I put my hand on her knee and then slid it up the inside of her stocking-covered thigh. Her legs parted as my hand probed higher, moments later my fingers were caressing the warm skin above her stockings. Annie sat back on the settee so that she became even more open to my caresses and I accepted the invitation by sliding my hand over her silk panties. As I almost expected my fingers felt a stiff erection that I grasped through the thin material of her knickers and as I did so I kissed her passionately.

"You don't mind?" she whispered when the kiss ended.

"Oh no," I replied and held her more firmly as she thrust her pelvis against my grasping hand.

"I think we'd better go upstairs," she said as she took me by the hand and led the way.

Her room was very feminine with a very large bed dominating the space. Standing at the end of the bed we fondled each other as Annie undressed me. Once down to my briefs she pushed me back onto the bed and then proceeded to do a very erotic striptease. First, the blouse was slipped from her shoulders and dropped to the floor, then her skirt, that had been holding my attention because of the obvious bulge in the crotch area, followed by her silky bra. At this point, she was wearing a satin garter belt, stockings, and satin panties. I couldn't wait any longer so grabbed her and pulled her down on top of me.

Even as we kissed our hands slid into each other's undies and I felt her hand grasp my erection at the same time my fingers wrapped themselves round her equally rigid prick. In my state of high excitement, it only took a few thrusts before I was squirting my spunk, and moments later Annie too was cumming over the both of us.

"God that was amazing," I said huskily.

"I know lover," she replied.

We stripped our briefs and tidied ourselves up. Then, pulling a sheet over ourselves, Annie, who was still wearing stockings, wrapped her legs round my body and we began to make slow sexy love.

I woke in the morning to the sunlight streaming through the window. Annie came into the room carrying two cups of tea. She was wearing the sexiest pale blue baby-doll pyjamas I had ever seen. It was long enough to reach the top of her thighs and although it covered everything, being so sheer, it hid nothing, certainly not the way her pert breasts with their nipples thrust forward in such a tempting manner. Also, I could clearly see her tie-sided bikini panties and the shape of her cock that they hid.

"Oh, you're awake."

"Yes," I replied. "Come here," and, once she had put the cups down, I grabbed her and pulled her down onto the bed with me. My hands slid down her sides and reached round to grasp her buttocks as I dragged her on top of me. As I did so I felt her hand grasp my cock and slip it between her thighs. At the same time, her hot panty-covered prick pressed against my belly. The silky feel of her baby doll nightie against my body was a wonderful turn-on as I rubbed myself against her.

"Take my panties off. I want you to fuck me," she said.

I undid the ties of her bikini bottoms and once free of them Annie rolled me on top of her and wrapped her legs round my back. I felt her hand guiding my penis to her bottom hole.

"Fuck me lover, fuck me," she husked.

I felt my cock head pressing against her ring so firmly pushed forward, as my cock slid into to her Annie gave a contented sigh. I began to fuck her and she responded by pressing her rigid prick against my stomach. In what seemed no time at all we both were at a fever pitch.

Annie suddenly gasped, "I'm cumming," and I felt her whole frame shudder as she shot her load between our bodies. This only served to bring on my own crisis and moments later I was spunking into her arse even as her legs pressed against my sides.

Once we had recovered she hugged me even closer and whispered, "God that was fucking great."

A little later, after we had showered, we were downstairs having a late breakfast. I was wearing one of her silk dressing gowns and for the first time learning the pleasure of being dressed in a sensuous material to the extent that I was getting stiff again. These feelings weren't helped by the vision of Annie in a very sheer flowing peignoir that, like her baby doll, covered everything but left little to the imagination.

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Halfway through breakfast Annie lent forward and asked, "Would you do me a favour?"

"Certainly if I can," I replied.

"My friend Sandy once said to me she fancied being fucked by a guy dressed as a girl."

It certainly wasn't what I expected but in the light of where I was, I barely hesitated before happily agreeing, saying I was up for anything Annie cared to suggest.

"I'm so pleased lover," she said, "I hoped you would be," and with that, she went off to phone Sandy. She came back minutes later and said that Sandy would be over in a couple of hours.

"So we had better get going," and with that, we were soon back in her bedroom.

I think Annie knew what she wanted me to be dressed up in even before she rang Sandy.

"If you dress as a maid you can serve us coffee before you serve Sandy," she giggled. She insisted I have another shower and shave all over, while she sorted out the costume she wanted me to wear.

"What do you think of this?" she said as she held up the black satin maid's dress for me to inspect. "I've had a lot of fun wearing it in my time," she added.

"I bet you have," I replied.

In no time she was lacing me firmly into a black satin basque, that had a small half-cup bra to support my nonexistent tits, and I found the feel of it quite arousing. Then a sexy suspender belt and some sheer black stockings that I eventually managed to clip the suspenders too. Again the new experience of wearing stockings and feeling their smoothness made me more aware of how feminine I was beginning to feel. White satin panties were next and my arousal mounted as Annie pulled them into place and made sure my cock was comfortable, giving it more than one friendly squeeze as she did so.

At this point she made me sit while putting a wig on. Annie had chosen a brunette one and the style was straight and long enough to reach my jawline. Some bright red lipstick for my lips and then she let me look at myself in a mirror. I had not been sure that I would look convincing so I was both surprised and pleased with the vision I saw.

"Aren't you a sexy siren," said Annie. I had to admit that the result was better than I had expected and I could feel my cock growing with my mounting excitement. I noticed that Annie's cock was also getting stiffer.

My dressing continued with a short ruffled half slip followed by the black wet look skirt and a separate top laced down the front covered by a frilly apron. Finally, some low heeled pumps because, as Annie pointed out, I had enough to worry about without learning to walk in high heels.

Then I sat on the bed and watched Annie dress. She slipped out of her peignoir and slipped on some crotchless panties followed by a short sheer slip. Annie was aware of my gaze on her semi-stiff prick poking through the slit in her panties.

"I like to be ready for anything," she giggled.

Then she put on a simple cotton skirt and blouse with some knee socks. All ready, we went downstairs and were only just in time for we had hardly got into the kitchen when the front doorbell went. It was Sandy, so I stayed out of sight, while she and Annie went into the sitting room.

I prepared the coffee and a few moments later, as we had planned, Annie called out, "Dee, can we have some coffee," This was the first time I was ever called Dee.

I tottered into the sitting room with the tray of coffees and, standing with my back to the girls, I bent over and put the tray down. My legs were spread apart when I did this and I knew my skirt with the stiff slip under it would spring up and reveal my panties and what they hid. I took my time before standing up and facing the girls and when I did so I noticed that Sandy's nipples were stiff little points pressing against her tight tee shirt.

"Isn't he lovely," said Annie.

"Is he real?" said Sandy.

"Oh yes," said Annie, "look," and with that, she lifted the front of my skirt so that Sandy could see my stiff cock that was barely hidden in my panties.

"Can I," whispered Sandy as she reached forward to grasp my hips, and by way of reply I thrust my crotch forward even as Annie said, "Well you once told me you fancied being fucked by a bloke in a dress."

"God yes!" said Sandy who, by this time, had my panties down by my knees and was kissing the tip of my erection. I responded by sliding my hands down the front of her tee-shirt and tweaking her nipples, while Annie unzipped Sandy's jeans and was pushing her hand down towards her friend's willing cunt. This led to Sandy sucking me and followed with Annie suggesting we continue in the bedroom.

I went up the stairs with my panties round my thighs and my cock pointing the way. Once there we pushed Sandy down on the bed and pulled off her jeans. I could see her knickers were wet with her juices, then they too came off. Discarding my shoes but still with knickers round my legs I climbed between Sandy's wide stretched legs and pressed forward until my rampant cock head was pressed against her honeyed slit. At the same time, Annie had lifted Sandy's tee-shirt out of the way and was sucking on one of her pert breasts.

Sandy pulled me towards her and there was no resistance as I pressed my prick against her clit prior to sliding into the hot embrace of her eager cunt. This was all she needed and she wrapped her long legs round me as I began to slowly thrust in and out. At the same time, she and Annie began to kiss passionately.

From the way she was lying on the bed, I could see Annie's little cock thrusting up her skirt. I lifted the skirt out of the way and gazed at her pretty upright projection poking through the slit in her panties. I grasped it and gave the tip a few licks before sucking it fully. It just seemed to be the right thing to do even as I continued to piston in and out of Sandy.

It certainly was the right action for moments later Sandy hugged me close as with a cry of delight she came, her juices soaking my cock, panties, and stocking. This set Annie off and she splashed my face with her cum even as I began to shoot my all into Sandy.

So ended the first part of Dee's confessions and I had to admit that I became very excited during the telling.

Indeed I was really enjoying the feel of the silk of my panties caressing my upright cock and was pleased to think that Dee had been photographing my obvious mounting excitement while she was telling her story. It also appeared to have had an effect on her too, because there was a definite projection in the front of her dress, so I walked over to her and, as I told her how exciting I had found her story, I reached down and gently grasped her erection through the thin material of her dress and knickers. Dee thrust her pelvis forward and I grasped her more firmly while my other hand slipped round her back and caressed her bum.

"I thought you were enjoying it," she whispered, and she kissed me lightly while running her hands up and down my back and hips. She slid a hand under my camisole and released my prick from my panties then began to stroke it even as she pressed herself against me.

I pulled her dress up and was now caressing her bottom and squeezing her stiffness through the thin silk of her French knickers. Soon we were on the studio's prop bed and Dee had me on my back as she stood between my outstretched legs with my vibrant erection in her hand. Before I knew it Dee's bright red lips were wrapped round my prick and, with increasing excitement, I watched her luscious mouth sliding up and down my rigid pole.

It did not take long before I reached my climax and I was squirting cum over her face and my undies. I pulled Dee onto the bed beside me and lifted her dress out of the way, I slid my hand inside the leg of her knickers and firmly brought an equally stiff cock from under its covering so as to return the favour. Moments later she was crying in ecstasy as she shot her spunk into my mouth and over her dress.

Dee took off her dress and we lay down and cuddled and caressed each other enjoying the pleasure of stroking the silky feel of our undies and the smooth skin they covered, all the while rubbing our stockinged legs between each other's thighs, that only served to get us ready for more fun.

"Paula, next time I want you to make proper love to me."

I knew what she meant and as before I could hardly contain myself.

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Written by 2Bkilnhill45
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