After inquiring about local customs, a boy is encouraged by his friends to appear as a pretty girl for a day.

 

A Stroll In The Park On Carnival Day

by Minnie

 

Although I've never felt a conscious desire for boys or men, I sometimes wish I could look enough of a girl to attract the eyes of an ordinary guy like myself. While I know it would be difficult to learn to gesture and walk convincingly like a woman, I'm sure I would know better than the average girl how to tease and indulge an admiring leg man to the limit. I've never been bold enough to get dolled up and go out on the street back where I live, but a couple of months ago I realized a friend of mine had a similar fancy. I never saw him actually do it, but he told me he did appear as a woman in public not so many years ago. His story captured my imagination, and I remember almost word to word how he told it, over a bottle of wine we shared in my flat one evening. Believe it or not, but this is what he told me:

 

" I was visiting my college friends in Germany. I was 25, slim and delicate enough to look good in a dress, and happened to be in a party with a mixed crowd of people when someone mentioned the coming carnival season. I had heard about the custom of cross-dressing during carnivals and asked if it was actually done during this one. My friends said no but then someone said: "Hey, isn't that a great idea!" I never told those folks it wasn't the first time for me, but at the end of the day they must have known I liked it more than I had let out.

There were three of us guys who wanted to dress up, and a couple of girls agreed to help with the preparations. One of them was Annette, a girl used to go the same college as I in the U.S. and who had since trained as a doctor. She came out of the pub together with me and suggested I walk her home. The evening was balmy and I wished I'd been more forthcoming about my crush at her back in the U.S. "What are you planning to wear for the carnival?" she casually asked me.

I was silent for a moment. In fact I was not serious about it and regretted that such a beautiful night saw me reveal my secrets. "To be honest, I'm not planning to. I was just asking since it's one of the more exotic things I've heard about life here. If I even tried dressing up as a lovely girl folks would think of me as a joke."

"That's not a good reason to chicken out now that you've talked all your friends into this. Plus, I think it is an appropriate thing for men to try it out, to find out for once what it takes from women to please men's wishes. And I can tell you get excited by just thinking about it", Annette answered.

I felt awkward knowing she had figured me out and took my time admitting that the thought did turn me up a little. At the end of our walk Annette invited me in her studio flat and told me she wanted to see if I fitted in some clothes she had.

"Just to convince you. I think that with the right preparations folks would actually mistake you for a girl. Notice we are about the same size – I am your only chance of getting through this and not looking ridiculous!"

Annette gave me a cup of herb tea and sat down to continue the conversation. "Before we go along I'd love to hear more of why you want to do this", she said. "I don't mean to ask whether or why it turns you on. I know that many men get a kick from wearing women's clothes and I have no problem with it. But if you were a girl you would not just dress up and walk the street in some sexy stuff – you'd think about what to put on and why. So, tell me what reasons could a girl have for wearing her skirt impractically short, or dressing in high heels and tight sweaters?"

Annette smiled at me while I thought what to say. "You mean, you think it's potentially demeaning for women if I want to dress as one, unless I know what kind of woman I want to be like?" I said. "Is that not stereotyping?"

"No, not like that – I just want you to think how you want others to think about you when you are doing it. What kind of messages would a girl's clothes give to those who are out there with her?"

I thought about it some more. "Maybe get everybody's attention? Short skirts would be one of the most efficient means for that", I said.

"You wouldn't want just anybody's attention, that's the problem", Annette said. "Think about a geek you'd never want to meet, and he has his eyes on you all the time. And you don't want to look like you are for sale. So, why do lots of decent girls still go out looking hot?"

"If you want to be noticed by somebody special. Or if you are on a date, and want to show to the guy you appreciate his company, maybe that's a way you give him something to be noticed for?" I said, after a moment of thinking.

"Don't you think that would just be playing up to the guy's wishes? That's a very male-centered idea, although it could be true sometimes', Annette said. 'But think about all hidden agendas that a girl might have, and how far would she really go because of them."

"Make the guy jealous, then?" I responded with less confidence.

"Well, that could be one reason. But imagine how it could also be fun for her, whatever the men think. Like being a little outrageous, looking sexy just for the hell of it. Or dressing up in a classy way to increase your confidence. The point I'm trying to make, it's more subtle than you think. Let's have you try on some of my things" she said, opening the door to a closet.

I dressed down to my underpants in the back of the room and pulled on the dress she handed me. "Not bad at all", Annette said when I turned back to face her. "Not enough to turn you into a woman, though. Take a look at my other things and see what would turn you on if you saw it on a girl friend of yours."

I looked around and saw a sleeveless linen dress which was blue on one side and purple on the other. At her nod I undressed and tried the new dress which was a lot shorter. Annette got up and handed me a matching blazer which covered my arms. "That's better, she exclaimed. "We just need to think how to get you to fill it out more. Take it off and I'll find you some underwear."

Annette rummaged in her drawer and took out a bra and a couple of flat cardboard packages which said strumpfhose. "Do you know how to put these on?" Annette asked, smiling at how nervous I hade become. It was far from the first time I'd tried on pantyhose, but Annette insisted on helping and demonstrated how you should first straighten the hose by inserting the hand in it. After I had awkwardly pulled on the hose and stood up, Annette helped me put on the bra and slip into the dress once more. She smiled at my new get-up and declared she'd make me a convincing girl.

"Men say they love it when you wear a short skirt. But you'll have to learn a lot about how to carry yourself in it. And do get rid of that hair on your legs and arms and wear dark nylons. And proper shoes." On saying this Annette rummaged in her closet and pulled out a pair of black suede Mary Janes. They were a tad small but I could put them on by stretching the band around my ankle.

Annette stepped back and took a careful look. "You look damn good" she said. "Care to take a look on your own?" I went in front of a large mirror next to the entrance of her flat and had to agree. "Now", said Annette, "the difficult part is not to make you look like a real girl, but to decide what kind of girl you want to look like. Think of that when you walk in the room and sit down with me."

I waited until Annette was standing in the only big room of her flat and walked in with a straight posture and short step. I even managed to smile to her and say hello with a chirpy voice before sitting down in a coach in front of her. I tried to keep my knees together and sit close to the edge, instead of sinking on the soft cushions. Annette's eyes followed my every move although she was not obvious about it. "Not bad", she commented. "You don't just want to be sexy but a little classy as well. You just have to keep that in mind whenever you sit down in that dress."

On the following evening Annette and a girl friend of hers gave me a crash course on how to walk and smile like a girl. While Annette promised to lend me the clothes and accessories it remained for me to get a pair of high heels, underwear and a wig. Since it was a large city and I did not know too many people I managed to do shopping which would have made me blush anywhere closer to home.

On the carnival day I walked to Annette's house and rang the bell nervously. Annette opened the door dressed in blue jeans and gave me a mischievous, encouraging smile. She took me to her bedroom to show me what she borrowed from her mom. It was a white, lacy piece of underwear, much like a swimsuit with adjusting straps and a bra. It would help shape my body more like a woman's, and with fillings it gave me breasts. I was already wearing my my new panties and black sheer hose, and I had tried to make my male parts inconspicuous by folding them between my legs. I redid that procedure in the bathroom before I awkwardly walked to Annette who helped me to put on her mom's thing, with some fillings, and tightened the straps. I barely dared observe myself in the mirror but Annette remained laid back and invited me to put on the dress.

"Unless you are chickening out again", she said, "I'll have you wear something classy but short!" Giggling and glancing back at me she handed me her selection from the closet. It was a simple, sleeveless linen dress which was blue on one side and purple on the other. With the dark blue blazer I wore on top of it I felt properly enough dressed to work in an office. The only problem would have been my hemline. It was on the short side even for a New Year's party.

To complete my outfit, Annette took me to her bathroom and made up my face after which she carefully adjusted my wig. I had tried make-up before but never had it done to me by another girl. This time I was totally transformed. I needed Annette to pull up the zipper in the back of my dress. She assured to me I'd be a hit, as long as I didn't trip in my heels or let all the world see my underwear.

Annette wore a dark hat and Bavarian-style leather suspenders over a white collar shirt and brown leather pants. Even in that hideous outfit she made the cutest young boy. She told me she would not want to compete with me for attention, and a couple of times she gave me her arm so she could walk me across rough pavements. As the others came and we went to find a suitable place for an after noon promenade and lunch, I saw Annette greet a guy I had not met before. Wanting to do my part as well as possible, I went to him and cheerfully greeted him by kissing him on both cheeks. "Hi, my name is Georgia. What's your name, cute boy?", I said in a slightly chirping voice which would make him think of a Barbie-doll. He played along and started to chat with me. I was secretly pleased when I found that he could not help looking down at times, even if I kept my eyes fixed at his. A couple of times, just after he had stolen a glance at my panty-hosed legs, I made a point of stopping in the middle of a sentence and smiling briefly. Girls had done the same to me, hinting I had been caught staring at their short hemline but leaving it to me whether I should feel embarrassed or smile back in mischief.

It was hard to remain oblivious about my outfit myself. With high heels my sheer legs looked stunning, and my dress was so short it barely covered what I had on under. A few boys were watching me and obviously getting off every time I leaned over or sat down. They were the youngest of the lot and I rather liked the idea of provoking them. One whom I knew from a previous party went speechless as I emerged from the car in my mini-dress and let him see the white panties under my black hose. I just smiled and walked up to him, stopping to take off my blazer which was a little too much to wear in the morning sun. The motion of my arms brought my already short hemline up just a little bit more, but even if I was showing some pantyhose top he stood too close for another peek at it.

I looked the boy into the eyes and asked him to hold my purse so I could store my blazer in it. This turned out to be a mistake since my assistant was too nervous to take a firm hold of the purse which yielded when I tried to tuck my blazer between the handles. To get the job done I bent over and reached down, with other, luckier boys behind me delightfully watching my short dress rise above the waterline.

Just as I was taking my purse back and smiled to the boy next to me I heard the click of a camera. I knew that the photo would show an embarrassing amount of leg and more. Seeing I did not have much to lose I asked the photographer to come aside with me. We walked around the corner to a yard and I climbed up the back stairs of the house ahead of him, chattering to him like a girl from next door. He could only swallow in response when I turned around to look at him from my heights. I struck several poses leaning this way and that against the rail and finally sat down on a stair with a confident smile. I suspect the photos did not come off because the boy's hands were shaking! To make it up for him I made sure that, even without the photos, he'd make out the lace pattern of my underwear.

Some other dress-ups in our company were sexy as well, but they had chosen to overdo it and wear things like fishnet stockings and black bra under a transparent blouse instead of being classy in the way Annette had taught me. I exchanged compliments with them all the same and went to try my charms on another boy who had just joined our company. His name was Peter and he was younger than me, kind of delicate, the type which raises interest in girls without realizing it himself. I flirted and joked with him but let others to do most of the talking. For a while I stood next to Peter in a girl-like posture, feet together and arms folded on the belly. As the group began moving towards a café I gave my arm to Peter and asked him to accompany me. I could see that he was glad to do this although he at first seemed shy and embarrassed, and sensing he was excited by my looks I wanted to lead him on.

My long legs stopped traffic as we walked towards a large, noisy café and lingered briefly on the door before entering. The attention I raised on the street was so much that when Peter courteously led me to the table I relished the opportunity to sit down and sip coffee. At this point I encountered one of the problems Annette had warned me about. Although I had pulled at my dress when I sat down its hem was riding up my thigh – well above the point where the weave of regular sheer pantyhose turns thicker and darker than the portion you usually see. I have never understood what purpose the distinctly edged panty part of nylons is meant to serve, unless it is to mark the absolute limit for short skirts. I must admit to a weakness for outfits which do not respect that limit. There is nothing sexier than a mini-skirt that casually drifts above the waterline. It remains a mystery to me whether women enjoy stunning a guy by this sight, or if men just get to enjoy it by mere luck. Some of my high-school classmates wore their skirts up to the edge knowing well that boys were always watching them walk up the stairs or sit down at their desk. Even so they were totally embarrassed when somebody actually saw a minor dash of their pantyhose top.

Now I knew how they felt. My sexy confidence turned to embarrassment when I noticed a man sitting at a bar side table staring at the highly exposed side of my thigh. To put a stop to him I had no choice but to get up again. In an unexpected move I turned to my friends and told I would get us all coffee from the bar. With a broad smile Annette said something, and in the noise I had to bend down to hear her. 'You could as well get this guy to buy you a drink since he's feasting his eyes on you even now', she said in the midst of giggles. She was circling my neck with her arm and speaking to my ear as girls will do while telling a secret to a friend in public. I had to bend down even more, and to avoid losing all decorum I quickly squat down next to her seat. I was mortified to think how much of my legs people had just seen. But Annette's laughter helped me regain my poise, and I got up and turned to face my new admirer.

As soon as the man saw me coming he turned his eyes away realizing his lady friend, her back to us, would soon find the reason for his lapse of attention. Determined to gain back the guy's interest I stood at the bar a few feet from him and leaned my elbows over the counter. The café audience behind me turned quiet from as my dress slid up and displayed a whistle of the reinforced part of my nylons. I waited for several seconds, allowing the man to fix his eyes at the top of my highly exposed thighs. My next move was to summon the bartender by casually reaching out to him. By waving my hand I deliberately allowed the hem of my dress rise up further, enough to give my new admirer a heart attack.

The bartender was serving others and I took a more casual stance, fiddling with things on the counter while I observed the man behind me from a mirror. I noticed a little brass bell and rang it to rush up the bartender. As I reached out for the bell my mini-dress revealed more leg than the café-goers had seen in a year, and the man behind me got a brief view of what I wore under the hose. The thought of it almost roused me as well. My glossy white panties were calculated to shine through thin dark tights, and flashing them in the artificial lights of the bar worked even better than doing it outside.

Knowing I had made the kill I turned around while the man was still absorbed in the study of my lower half. Embarrassed he looked away, unable to hide the bulge in his pants. On this moment of victory my purse slipped from my shoulder and fell on the floor. To avoid showing my panties a second time I hunched down to get it. When the purse was again hanging from my right shoulder I instinctively held my shoulder up so the strap would not slip off again. A moment later, when it was time to pay, I had to reach inside the purse for money with my left hand. To do so I had to twist more than my short dress allowed, and while I dug for another coin for the waiting bartender my dress revealed an indecent length of nylon-covered thigh.

I looked up to my friends further out with the reassuring smile of a girl who knows she's a bit out of line. From Peter's alarmed expression I knew the guy behind me had just enjoyed another close-up of my pantyhose top. I stuck to the bar while the bartender walked to the far end of the room to bring my change. Thinking it was time to even things up between Peter and the other guy I took the tray with four cups of Cappuccino to our table. I walked back with a waitress-like gait to stand and wait at the bar. Giving the bartender an impatient look I rested my elbows on the tall counter to lean on it and relieve the strain from my feet which already felt tired after an hour in high heels. I would lie if I said I didn't know this raised my shoulders, and my dress too, giving my boy a long look above the waterline.

 

When I got back to our table I sat down casually opposite to Peter, a couple of feet away from him. He gave me an awkward smile and turned towards the others who had joined us in a weak attempt to keep his eyes away from my legs and mini-dress. This was very difficult for him because we were sitting face to face and the table was so little it hardly blocked anything from view. Turning to the others I followed the conversation also, aware that Peter would see all the way to the shop as soon as he glanced back in my direction. I let him look up my dress all he wanted, amused at finding how often his eyes were drawn to the seam of pantyhose spanning my crotch.

Peter must have taken a long look up my dress because Annette caught him doing so. "You guys look such a good match", she chirped to him. "Why don't you take a little walk along the river so we can admire you together?"

I was game and stood up, giving my hand to Peter who put up an embarrassed smile as he joined me on a promenade to a riverside park near the café. He did not say much along the way but did not object when I brought us further away from people. As soon as we were no longer observed by our friends, he became more relaxed and finally complimented my appearance. 'How does it feel to be so gorgeous?' he jokingly asked glancing down at my legs. 'Why, thank you', I said. 'I have secret advantages that you haven't seen'. I feigned pride and touched on my chest with both hands and made a flourishing turn around in imitation of a fashion model. Then I gave Peter my hand and he took it, and we walked along for a few steps until he gathered enough courage to stop and hug me. A moment of that and we were kissing. Peter's wandering hand made shy caresses at the small of my back and my bottom. In my heels I was a little taller than Peter, even if I spread my legs slightly to make up the difference. His dick hardened when I got closer to him in response and for a second it brushed directly against my crotch under the short dress. I withdrew before the thought got too exciting and we walked on, still holding hands.

We passed some white rose bushes growing next to the path, and I told Peter that for his shameful advances he should give me a flower. I walked over with Peter to show which flower I liked, and he knelt down to carefully extract it from the thorny bush. I was actually giving him an opportunity to steal another look up my mini-dress. To avoid being stuck in the grass in my high heels, I had to keep one foot on the path and step towards the bush with the other. Peter was squatting next to me, and with my legs stretched apart he only had to raise his eyes to see the crotch of my pantyhose which had slipped down to the level of my hemline during our walk and other exercises. Peter took his time with the flower and pointed at various objects in the scenery, admiring them to me aloud while he kept looking up at my legs. Eventually he had the courage to lay his hand on the inside of my thigh. He did not put it outrageously high, as I first thought, but he was still able to reach up his finger and secretly touch my sagging nylons at the seam. Before I knew it he was twisting or pulling at my hose there, so cautiously I barely felt it slip further down along the smooth behind of my panties. I let Peter carry on for a second, but before he had time to touch anything else under my short dress I stopped him casually and bent down to examine the slack in my pantyhose.

I did not make a fuss about Peter messing up my outfit but warned him about the thorns in the bush. Having directed his attention back to the roses, I swept my hand along my thigh up to the spot where Peter had fooled around. Finding the crotch of my hose way down from where it should have been I stepped up, told Peter to not peek and started adjusting it. Turning away from Peter I used both hands to pull at each leg of my nylons, and finally the top, to make them fit all the way up. Although I tried to work under the cover of my dress I hadn't had much practice in this procedure and could not help showing off my white underpants before I could properly tug down the hem of my skirt. I turned back to receive my flower from Peter and found him even more tantalized than the guy in the café. Nothing about the roses or the river could have made the boy so pale in the face.

Things were getting so serious I decided to grant Peter more favors. I took his hand and brought him to sit on a park bench surrounded by rose bushes. He remained there watching me as I walked back to the place where we had stood in order to look for my purse which lay on the grass. I bent down to leisurely pick it up, even as Peter was riveted by the sight of panties under my mini-dress. I got up and smiled and passed my hands under my long hair. He had relaxed and did not even try to conceal the bulge in his pants. I put my purse and the flower on the bench and remained standing a couple of feet away from him.

"Do you think I'm pretty", I asked him as he looked me over. I spread out the hem of my dress with one hand, smiling at him teasingly. We both knew that my dress was not long enough to cover the reinforced top of my hose when I did this. Peter reached out and put his hand under my dress, stroking me through my underwear. I was getting stiff and wet all over the place, but this time I let him go on.

"You know", Peter said finally, "I used to have a fancy for Annette when she wore that dress. I was just imagining you were her".

"I'd love you to think I'm Annette", I said. "What would you like me to do?"

"Could you stand in front of me and do what you did in the café" he said, getting white in the face again.

I told him to wait and turned my back to him, bending to lean against the handrail at the far end of the bench. Now Peter saw from close up what the man had seen in the café, and I could hear his breathing get heavy. I heard him zip his pants open. The long hair of my wig covered my face from him, and I did not turn to look at him but just heard his breathing get heavy. His hand moved pleasantly along the inside of my nylon-covered thigh until he was stroking my behind with his hand. I was afraid it would tickle me but he touched me firmly and evenly and I rather enjoyed it, as I concentrated on nurturing his excitement. Strangely enough I was not getting hard myself. I wished for a moment I were in Peter's position, but when I simply let him have his way with me I also felt myself withdraw as if I were a spectator.

Suddenly I was concerned about passers-by who, thankfully, had not appeared so far. I realized I'd still have to appear in public in my dress and held it up in the front to avoid any stains. In my purse I had handkerchiefs and spare nylons which I would change into as soon as I found a ladies' room, but I was concerned the run in my hose would show a mile away before I got that far. Peter looked spent but euphoric as I rearranged my dress, and scarf. "How's my make-up", I asked him and got an advise to wipe off some mascara from my cheek.

When we came in sight of our friends who were walking towards us on the path I realized it wasn't enough to get back my own poise but also to get Peter to swagger. "Quickly, Peter", I said to him, "let's walk straight to them, and tell me a joke to make us both laugh!"

We pretended as if nothing major had happened, but Peter was not very good at telling jokes to a crowd, and I suspect others could also sense that his legs had become like spaghetti. So were mine, for that matter, after a couple of hours in high heels in which I had little practice walking. We went to sit down in another café, for a while, but then Annette rescued me and took me back to where I was staying. Peter and his friends said their goodbyes in unison, and I did not see them before, but I met Annette to return her the clothes I had borrowed and say my goodbyes a couple of days before my trip home. She was quite interested in hearing how I'd liked being a girl.

"I loved the attention", I said.

"You looked very cute", she responded. "If you go on with this, I'll have to worry about competition".

With some hesitation she went on. "Care to tell me how you got Peter so excited? You know, I'll have to do something that matches up with it next weekend."

"What do you mean", I said. "I gather he liked a lot what he saw, but he'd have wished I was a girl."

"Luckily you weren't. You see, he and I have been together on and off, and I promised to go on a date with him after this is over."

  

  

  

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