by Richard Large

Raji's note: This story came to me from a friend. I enjoyed reading it and I am sure you too will. I made a few changes, which I could not confirm with my good friend's as her e-mail does not seem to be working anymore.

I looked into the mirror and began removing the makeup from my face for the third time. What was it about doing up the face? It seemed that no matter how carefully I worked with it, I just could not make it happen. To start with, I didn't have the knack of working on my reflection. On top of that, when I was trying to put the damned eyeliner on, my hand came in the way and I could not see what I was doing and it was frustrating. I took a deep breath and leaned back from the dresser mirror. I needed to relax a bit before I started once again.

After composing myself, I began again, maneuvering the little brush around the line of my eye. I finished the right eye. It looked pretty good - not perfect, but good enough for a beginner.I finished the left eye and studied the effect carefully. I decided to settle for it.


I was putting on the lipstick, trying desperately and quite unsuccessfully to keep it only on my lips when my sister's voice carried up the stairs. "Jerry! Heather is here!"

'Oh shit', I panicked.

Desperately, I tried to prevent her from coming up. "Uh - okay - I'll be down in a couple of minutes!"

But it was too late. The sound of her coming up the stairs made my heart jump into my throat. I didn't want her to see me like this. I threw my bedroom door closed, wishing it had a lock. But no such luck! The door opened smoothly to expose me.

Heather was in.

She took in the sight of me standing in my sister's bra and panties with the half-finished makeup on my face. Her own face showed surprise? mischief ? irritation ?... A little bit of everything perhaps.

"Why aren't you ready ?" She glanced at the pile of makeup littering the table by my bed. "Honestly, women!" It was a perfect parody of the line repeated so often in movies and sitcoms, but this time it didn't strike me as funny. "What is taking you so long? You look a mess," she said in mock anger.

"It's this blasted makeup," I huffed. "I don't know how to put on this stuff and have it look good."

Her look became one of amusement. "You poor thing, no one has taught you to put it on properly, have they?" Her tone was patronizing, but her attitude was all business. "Well, I guess we'll be a little late to the party, but I will help you with this. First thing is to scrub all this mess off you." She turned my face to the light, picked up a tissue and dabbed it in the cold cream, then began swabbing my face with it.

"It is all because of you", I complained, as she wiped my face clean," I wanted to go as a cowboy, but that was too common for you. No - nothing would do, but for us to go as man and woman - you the man and me the woman." I made a face. "Anyway, I guess this proves I'll do anything for you, Heather."

She smiled and kissed my forehead. "That's best part of what I love in you, Jerry."


"Well, you do have nice pert breasts," she joked as she caressed one well-filled bra cup with the palm of her hand and gave me a look which said she knew that I was enjoying this attention.

"Gee thanks." I smiled. But I wasn't about to admit how much it turned me on.

"Now let's make you nice and pretty in other ways as well." Heather crouched in front of me and began applying the makeup. She cupped my chin in her hand and spoke softly to me as she worked, telling me what she was doing each step of the way. But her voice became a pleasant droning background to the new sensations that flooded me. I reveled in the sensations of the various brushes and pads against my skin and the firm way she moved my head this way and that.

"Why, I believe you are really enjoying this." The meaning of her words slowly sank into my consciousness. I opened my eyes to see her gazing thoughtfully at my arousal, evident through the flimsy fabric of my sister's panties. She kissed me gently on my cheek as she lightly brushed the growing evidence with her finger tips, causing a new shimmer of pleasure to course through me. I closed my eyes again and she continued with the makeup.

"We' re done," she chuckled. I opened my eyes, and saw the strangely excited light in her eyes. It seemed to match the strange feelings within me.

She appeared to struggle briefly before she composed herself and led me to the mirror over my dresser. I was astounded. She had made me look stunning. I turned my face right, then left, studying the effect. It was a marvel. I was beautiful! My cheeks were pink. My lips were deep red. My lashes were full and I even had shoulder length hair.

"Now I'm jealous," said Heather though she did not look in any way upset. "My boyfriend is prettier than I am!" she said and her smile was as gentle and loving as I had ever seen it.

She helped me with the clothes - a dark skirt and orange top. It was borrowed from my sister. I think that made me look sexier. Another trip to the mirror told me that I had become a lovely teenage girl. I felt a mix of pride and... ...something else I wasn't sure I wanted to identify. Instead of exploring my feelings, I studied Heather.

She too looked convincing. The slacks and bulky sweater hid her slender build, and the way she had swept her short hair was, indeed, masculine. The little stubble on the face completed the illusion. Heather came up from behind me and we looked into the mirror and saw ourselves as a nice couple. I was convinced that anyone who did not know us would naturally assume that she was the guy and I the girl. Wasn't I glad that we were of the same height, as she hugged me and kissed me gently on my lips. It felt good as my breasts pressed against her. I closed my eyes and enjoyed the sweet sensations passing through me. I felt happy and we were smiling at each other as we went downstairs arm in arm.

As we reached the main door, Gina spoke from the hallway. "Hang on guys. Don't want to let you get away before we commit this event to posterity!" We turned to see her, caught the flash as her camera recorded our happiness. "That one's no good," she frowned. "Jerry, put your arm around Heather's waist, and Heather, put your arm over Jerry's shoulder." We complied and she took a photo. She went on to click eight or nine pictures of us, in different poses, before she relented and let us get on our way.

In spite of my fears, we were not particularly late to the party. Several people had arrived before us, and we found ourselves stopping to talk to many of them on our way back to the kitchen where the drinks had been set up. I found myself falling into my role naturally, and Heather seemed to have no difficulty either. I was quite pleased when a few people we didn't know, asked why we weren't in costume. I lowered my eyes and smiled shyly while Heather grinned at them without answering, as she draped her arm across my shoulders in a possessive way that I found to be nice.

As I reached for a beer glass, Heather touched my hand, her eyes smiled and she shook her head, just a little. I understood her signal as she began mixing a cocktail for me - something elegant and feminine looking. I sipped it and found it a little sweet, but quite tasty. When I saw the trace of my lipstick on the edge of the glass, I felt a subtle twinge in my groin. I sipped again while I looked into Heather's eyes. She leaned forward and embraced me softly as she kissed the side of my neck. A sexual charge surged through me, and my knees grew a little weak. Recalling the phrase I had heard so often from her in similar situations, I whispered, "please...not here."

Slowly, we found our way back through the crowd to the living room and found friends we could hang with.

With time, the crowd grew larger. Fortunately, most of the people here were folks I had never met before. I was apprehensive at first - afraid that someone known would mistake my costume for evidence of a less than macho attitude, but I found my concerns baseless for more than one reason. Most of the people did not know I was a guy, even some of my friends did not recognize me at first. And even those who did know did not seem concerned - this was, after all, a costume party. Everyone was expected to be in the guise of someone they were not. There was a moment with William, one of the football team who got belligerent when he figured out who I was. He made some kind of crack about faggots but his girlfriend snapped at him told him to stop being stupid.

But the incident did make me think. Although I had started the evening in the guise of someone I was not, I found myself enjoying what I had become - finding a certain comfort in this disguise. William's crack made me analyze my feelings, and what I realized about myself surprised me. I enjoyed being a girl and I enjoyed having Heather as my man. I enjoyed the little loving gestures my man made to me. I also felt a little fear in the pit of my stomach as I analyzed myself and I held Heather's arm tightly.

Heather, my friend for years, before we started dating, was sensitive to my moods. She sensed right away that something was bothering me, and guessed what it might be. As my man now, she steered me through the back door into the garden. There were little lights strung among the trees and bushes and a path that led a short way from the house to a bench by a small fish pond. We sat on the bench. Heather turned to me, took both of my hands in hers and looked into my eyes with sympathy.

"Are you disturbed about what William said?" she asked softly.

I was hesitant at first, not sure how far I could go with her, not sure if I wanted to risk our relationship by revealing my feelings. As she encouraged me to talk, I admitted what both of us already knew sub-consciously - that I enjoyed the roles we were in and that I wanted to do this again. I said that and watched her face for the reaction. Her face softened as she said, "I want it, too," Her voice was husky with emotion as she said it.

Her arms found their way around me, embracing me. I had tears in my eyes and my surroundings became hazy. My lips found hers and we clung to each other in a soft and lingering kiss that promised so much.

I giggled nervously as I wiped the lipstick from her lips and the tears from my eyes. "Can we go home now?" I asked.

"My house is closer, and no one is home," she responded, squeezing my arm and giving me a peck on the cheek. The implied promise made me giddy with anticipation.

I don't really remember leaving the party. I do recall arriving at her home, entering the front door and moving into her arms right there in the front hall. I remember clearly the kiss, her tongue exploring my mouth, her hands exploring my body. I recall going limp with desire before she released me. I know that I caught my breath as she led me up the stairs to her bedroom, then lost it as she closed the door and caught me in another embrace.

Without being aware of moving, I found the edge of her bed touching the back of my knees, and I sank down, pulling her down on top of me. Her lips never left my mouth as her hands found the hem of my cheerleader's sweater. We broke the kiss just for a few seconds, as she lifted the sweater over my head.

Then she unfastened my skirt, and slipped it down my body as I raised my bottom to make it easy. I caught at her as she stood up, but relented and watched as she took off her sweater and slacks, returning to me wearing only her moustache. Her hands explored my soft skin while her lips explored my mouth, my face, my neck, my shoulders.....

She slipped down my body and drew the panties away from my quivering cock, kissing it lightly on the tip before she engulfed it softly with her mouth. Before I lost control, I pulled at her shoulders, urging her up on top of me, and she agreed. After kissing my lips and squeezing my bra one last time, she climbed over me and captured my hardness with her wet sex.

"Oh, sweetheart," she whispered, "I will always make love to you like this."

"And I will always be your girl," I promised. "But fuck me now, my dear, fuck me and make me come like I never came before!"

And she did just that. Slowly and sweetly at first, then wildly. At the end, she was gasping and sweating much more than I was. I watched her boyish face as she fucked me, her eyes sometimes closed in concentration, sometimes open and drinking in my own pretty face and body. And when I felt my orgasm building, I urged her to make me cum, begging her to cum with me, and she did, shuddering sweetly as my spunk lubricated us. This was completeness - she and I together, loving and straining to be one. The warmth that had built in us so urgently blossomed and settled like a slow bubble around us and we swayed sleepily in each other's arms, still joined in our bodies, unable to find enough energy to do much more than look into each other's eyes and fall asleep.

That was last night. I am awake now as the day is breaking, still in her arms, the dried evidence of our passion crusting skin and sheets. Her face is so serene in sleep, my head is on her arm, but now I have to go pee. The makeup on my face is itchy and I want to get it off. Though I want to clean it off now, I know I will want her to put it on me again - and dress me up in the prettiest of dresses. I also want to choose the dresses which will make her look handsome. You know Heather is now smiling in her sleep. Maybe she can read my thoughts.