Juliette ...

And then he was a she

My first outing was at a party on the theme: "Outrageous!" Yes, with an exclamation mark. A group of gay men had shared a house, their lease was up (or were they under threat of eviction?) and a party demanded to be thrown.

At the time I was dating a girl, Juliette, who worked as a shop assistant with one of the housemates, and she was very excited at the prospect of going. Until it came to the problem of dressing me up. She wanted me to rent a fake uniform and get all the gay boys hot and bothered (fine by me) but the cheapest uniform-rental was still far too expensive for my university-induced insolvency.

Things were looking pretty grim - it was the day of the party and no outfit had been planned for me. "So what are you wearing, then?" I asked Juliette, who immediately began to describe the outrageously pink, tight, cleavage-displaying and just-below the crotch shortness of the dress she'd borrowed... and then she looked me up and down, face illuminated with the maniacal glee of perverted genius. "You know, you've got great legs!" Somehow this didn't particularly give me any comfort, the way she said it. Juliette was short, petite and brunette.

Her half-sister Justine was tall, curvy and had big feet. So we started with the shoes. It all hinged on the shoes - if she could get me into a pair of heels, worn with my own suit and a tie, I'd be properly outrageous, but in a discreet sort of way. Rummaging through her younger sister's shoe collection we found the prize find that was a nice pair of brilliant pink 4-inch heels. One small step later I was on the floor. After three more attempts at walking I was seriously considering gagging Juliette with a pair of Justine's tights. (Come to think about it, in retrospect I think she'd have loved it).

After a few more affronts to my dignity the balance improved, and by the time I learned to put some swing into my hips and allowed my body to accept the position that the heels forced it into, I began to do just fine - I sauntered, baby! That's when Justine came home, took one look at me in those heels and gasped "Omigod, I've got the perfect dress for him!" Juliette squeezed me into this tight, blood-red number with almost no fabric around the back, and a front that was held up by the collar - no straps. So my chest was fully covered in shiny, tight fabric, and my back and shoulders were exposed - their squareness exaggerated by the feminine shape of the dress. It did show off my legs, however.

The sisters made sure to point this out to me after they solved the obvious problem of my utter lack of man-breasts with a padded bra stuffed with sundry items out of Justine's sock drawer. Having done that, they of course wanted me to put on a pair of control-top tights to give me some curves. And shave my legs. I cooperated fully, even when the pair of them stood behind me, critically evaluating the visible panty line on my bottom - or rather, the visible jockey-shorts line - and declared that I could only pull this off if I went commando. I even sat still and had my face made up in a style that I can only describe as a cross between brazen hooker and Duchamp's "Nude Descending a Staircase".

The sisters, by contrast, looked hot. Short very short dresses, tight very tight tops, high extremely high heels, glimpses of stocking top and lacy bra straps, red lipstick, and enough hairspray to necessitate a toxic cleanup in the morning. We sure made an entrance at the party. Unfortunately for my drinking, I realized after my first glass of poisonously alcoholic fruit punch that my newfound talent for walking in stilettos didn't quite hold up under intoxication. So I held off on the drinks, while everyone else who wasn't worried about getting intimate with the pavement got blotto. One thing I hadn't anticipated about going out in dress, pantyhose and nothing else, was the trouble on the dance floor.

Juliette and I were wiggling away to some hilariously gay dance music, when suddenly she stretched up and whispered in my ear: "You've got a hardon, babe." As if I didn't know. But without the constraint of my normal jeans and shorts, there was nowhere for the erection to go but out - pushing the skirt up and out right there front and center for the world to see. I pulled Juliette closer to hide my condition, and she giggled naughtily, rubbing up against me, doing nothing to alleviate the situation. "What are you doing?" I asked. She was wearing the hot pink number that had started this whole thing off. "Making trouble," she giggled. "What are you going to do about it?"

Without answering I took her hand and pushed her in front of me out of the living room, up the stairs, and into a bedroom I had noticed earlier was full of packed boxes, neatly stacked. We kissed, hungry, rushed, and I pushed her up against a stack of cartons that began to wobble dangerously. "We've got to get back downstairs, someone will notice..." she whispered, while at the same time her hand was reaching under my skirt to rub my hard cock through the pantyhose. "Well, then, since you got me into this, it's your job to keep me looking decent before we get home and I can fuck your brains out properly."

Juliette smiled and crouched down in front of me. Stroking my smoothly shaved thighs she pushed the dress up and began to nibble at my cock, the nylon between her teeth and my cock. She pulled the fabric down, releasing my aching shaft out of the tights and took it in her mouth eagerly. It was a rushed, furtive, quiet blowjob, and I could tell from the way she took me in her mouth she was simultaneously turned on and horrified at the thought of someone walking in to see her crouched in front of me, sucking me off while I held my dress up in front of me. I managed not to gasp as I came in her mouth. In the half-light I noticed that she had left red smudges of lipstick on me, up and down the shaft. We reapplied some lipstick, powder and mascara in the half-light of the room. I was daubing my lips with red, very carefully, when Justine stomped in. "Where have you been?" she asked, suspicious. "The bathroom was occupied, we had to fix our makeup."

"In the dark?" I flipped on the light. The one bare bulb dangling from the ceiling did us no favors. This is the problem with girls like me you don't want to look too closely. A while later, when it was time to leave and I had been discreetly stroking and fondling Juliette, impatient to get her spread-legged in bed so I could thank her properly for the night out, she nudged me with her elbow: "I don't like the way those boys are looking at you - let's go home." Outside I had the best luck ever hailing a cab. We were halfway to Juliette's place when we realized we'd left Justine back at the party. "Should we turn around?" she asked me. I pulled her hand to me and all the way up my dress. "No, I don't think so."