How Kim Humiliated Me In Drag             by: Cissy Gaye

 

This is the story of the first time I dressed in drag in front of a GG (genuine girl) and how I inadvertently put myself in the position of being humiliated in public. This was the early 1970’s, when glam rock was big and magazines like Creem regularly featured guys in very feminine attire if not outright drag. Among my friends was a girl - Kim - a mischievous brunette with a wicked sense of humor. I was in a record store one day with Kim and she brought up the subject. She showed me the covers of some records that featured boys in fem clothing and then she said, "You know, you’d look kinda cute in a dress, I bet."

Well, I was very excited at the thought, as I had been dressing for years but I’d never confided that to anyone. So, casually, I mentioned that another friend, Melissa, had recently said it wasn’t fair that women could wear skirts & pants but men could only wear pants. I told Kim how I had assured Melissa, who everyone knew I had a crush on, that if she would marry me, I would be glad to address this inequity by wearing the wedding dress. Melissa had promised me that if we did indeed marry, she’s be glad to wear the tux and she’d love to see me in the wedding dress. We had laughed it off, but Kim said that she thought it would be fun to dress me up sometime to surprise Melissa. I said okay, figuring nothing would come of it. Shows what I know.

A few weeks later, I was driving home from a club and as I went by Kim’s house, I saw her sitting on her front stoop. I stopped and joined her. She told me that her parents were away in Europe and she was waiting for Angela, who lived around the corner, to get home from a date. Kim confessed that she didn’t like being in the house alone and planned to sleep over at Angela’s.

Before long, the conversation turned to my casual agreement to let her dress me as a girl. "We’d have to practice before we could do it for Melissa," she decided. It was only about midnight and Angela wasn’t expected back for several hours. "How about now?" she asked.

I was terrified. I wanted to do it so badly, but I was afraid of the story getting out. After I extracted a promise from Kim to keep our escapade a secret, I "reluctantly" agreed.

"Great!" she said and she dragged me into the house. She made me strip to my shorts and, looking them over critically, decided Fruit of the Loom wouldn’t do. She was much too tiny for her underwear to fit me, so she got a pair from her mother’s room. Now Kim’s mother was an exotic Latina with an incredible fashion sense and the panties Kim liberated from her dresser were silky lemon yellow with rows of ruffles across the backside. "They’re called rhumba panties," Kim told me, then she turned around so I could change. As I was changing, I looked up and saw her peeking. "Aww," she said, "look at how tiny your little dick is."

I was mortified. I had, at best, a two inch dick and was very sensitive about that fact. Kim dissolved into giggles as she watched the blush color my face. I yanked the panties up to cover my lacking manhood, which was getting hard from the humiliation and she pointed to it. "Oh look, it’s waking up now."

We stood there for a minute or two - me with my little dick rising in the silky yellow panties and her watching and giggling. "What’s next?" I asked. She thought for a moment, then took a short frilly nightie from her mother’s closet and handed it to me. "Here. This should keep your little problem covered up while we do your makeup."

The way she leaned on the word little made it plain that she knew how humiliated I was and how much she was enjoying herself. I’d always sensed a kind of casual cruelty in her mother’s imperious presence and I could see now that it had been passed on to her foxy daughter. I put on the nightie, which was green and had ruffles on the straps, the bodice and around the hem. "You look adorable!" Kim said, laughing out loud now. I attempted a feminine pose and she laughed even harder.

"C’mon, let’s do your make-up," she said, pulling me into her bedroom. For the next half hour we sat on her bed as she transformed my face. When I was allowed to look in the mirror, I was astounded. She’s really piled the make-up on and I looked like a cheap whore. "Isn’t it a little...slutty?" I asked.

"The look suits you," she said cruelly through her laughter. She went to her closet and pulled out a silky mini-skirt with an elastic waist. It was a black and white print and had a flippy, flirty hem. "This is the only thing of mine that might fit you," she said. "We’ll get the rest from my Mother’s room."

"Your Mom might not like that," I said.

"She’s got so much stuff, she’ll never notice. We’ll just pick something she never wears anymore." A few minutes later she showed me several blouses. I instantly knew I wanted the white crepe blouse with the cascade of lacy ruffles down the front and the big lace-trimmed ruffled cuffs. I’ve always had a thing about white ruffled blouses, but I didn’t want to make that obvious. I pretended to look them all over then chose the ruffled one on the basis that it would help me look more feminine.

"Wait," she said. "You need a bra and a slip." She pulled a yellow bra out that seemed to match my rhumba panties and she motioned impatiently for me to cast off the nightie. Once she had it on me, she stuffed the bra with panties from the hamper. "This way she’ll never notice, cause they have to be washed anyway," Kim decided. The aroma from them was intoxicating. Kim checked them as she put them in and when one proved to have a skid mark, she teasingly wiped it across my face, laughing at my reaction.

"What?" she said in mock anger. "My Mother’s shit isn’t good enough for you?" Then she rolled the panties up and put them in my bra anyway. Then she chose an incredible white nylon slip with several inches of lace at the hem and a lace covered bodice. She helped me into it and as it fell down over my body, I could barely suppress a sigh of ecstacy.

"That little guy sure is having fun," Kim pointed out, delighting in my cock’s tenting of the slip. "You’d better do something about that."

"How?" I asked, feigning confusion.

Kim reached in the hamper, handed me another pair of soiled panties and said, "I’ve always wanted to watch a guy jerk off. Consider it part of the price of me dressing you up and not telling. I get to watch you."

"In these?" I asked incredulously.

"Sure," she said. "I saw some guy do it in a porn movie. You do know how, don’t you?"

My embarrassment over that had her laughing again and so, utterly humiliated, I went into her bedroom and, lying on her bed, with Kim sitting beside me eagerly watching, I jerked off. It took a while to get over the weirdness of the situation, but I finally got it going and when I came, my jism jetted out from my dick onto my thigh.

When I dressed up at home, jerking off was always the end of the ritual. Cumming turned off the switch that made drag pleasurable. The humiliation was no longer pleasant and I would pull off the clothes in shame. I told Kim it was time for me to change back, but she wasn’t listening. "Nonsense," she said. "We’re just about done and I want to see the full effect." But she didn’t make a move. She just stared at the pool of cum on my leg.

She finally put her finger out, scooped some up on her nail and tasted it. "Not bad, " she said. "Here, you try." She scooped up more and held it to my mouth. I shook my head. "Part of the deal," said Kim. I knew I was screwed so I took it in my mouth. It tasted weird, salty and pungent. "Want some more?" Kim asked. I shook my head again, but she just looked at me and I opened my mouth. We sat there for a while as she fed me my cum, then wiping off my leg with the panties, she said, "You need stockings."

Stockings meant a garter belt and then a pair of her Mom’s strappy sandles, which didn’t fit, but were close. She combed out my long strawberry blonde hair and used a long black and white zebra-striped silk scarf, headband style, to pull my hair back behind my ears, She positioned the scarf’s knot over my left ear, so the ends flounced around in my peripheral vision as I moved, tickling my ear. She took another black and white abstract pattern scarf and knotted it around my throat. "Male prostitutes who dress like women wear scarves around their necks to hide their Adam’s apple," she said. "How about it? Ready to go out and turn some tricks?"

I struck a hooker pose which made us both laugh, then she had me put on some earrings with tinkling bells hanging down. When I said the bells were annoying, she shrugged. "The only clip-ons I have. Would you rather I pierced your ears?" I shut up. Then she had me put on the mini-skirt. It failed to cover the slip by several inches. "I never thought I’d be saying this to you," she giggled, "but your slip is showing." I asked for a different skirt but she refused, saying there wasn’t another that would fit me. "Besides," she said, trying not to laugh and failing, "I like this look on you." She made me practice walking until she was satisfied with my wiggle, then she showed me how to sit and smooth my skirt out and then she announced we were going to take a little walk. "I can’t go outside like this," I gasped.

"Of course you can," said Kim. "besides, part of the deal, remember."

"No, I don’t remember. Seems like whenever you want to make me do something I don’t want to do, it becomes part of the deal."

"I know," she giggled, "and there’s not much you can do about it, is there? Unless you want me to tell..." So we went out. First, we sat on chairs in her backyard, but then she insisted we walk around the block. At the corner, she snatched some flowers from a bush and put them in my hair. She made me mince along and teased me about how I looked, how my slip was showing and how funny it would be to dress me up this way for Melissa. She kept leading me further away from her house. When I said I’d go back alone, she reminded me the house was locked and she had the key.

Finally, we reached a major intersection. There was almost no traffic at that hour. So Kim designed a little task for me to humiliate me even further. She made me go out in the middle of the avenue, do a little dance then flip my skirt and slip up to show my panties. The first couple of times I did it I got back to the sidewalk without any traffic coming by. But the fourth time, just as I did it, a truck came along and the driver tooted his horn appreciatively. I was so embarrassed and so turned on, it was overwhelming.

After she stopped laughing about the look on the trucker’s face, Kim pulled a scarf out of her pocketbook and insisted I let her blindfold me. Then, as cars went by, she flipped my skirt and slip up and flashed my panties. I could hear horns honk, but after a carload of guys went by yelling and hooting, she led me quickly down a side street. She took off the blindfold after a few blocks of helping me stumble along. At one point, she grabbed my replenished erection and led me by that, making a comment about how men would always follow their dicks. How true I now knew that to be.

We finally reached her house again and sat on the stoop to rest our feet. Mine were particularly sore as I was walking in 3 inch heels on shoes that were too small. I was just about to ask her to let me in to change when a car pulled up in front of Angela’s house.

"Oh shit," I said, "they’re back. C’mon Kim, let me get inside and change."

But Kim, who could really play the ditz sometimes, said she couldn’t find her housekey. I was really panicking now, because I knew the guy Angela was dating was a real Cro-Magnon type and I did not want to be seen by him (or Angela for that matter) in drag.

Kim kept dithering about the key, and then the car doors opened and Angela and her date got out and started WALKING TOWARDS US!!!!!

I came down off the stoop and ran around behind the house. Once there I walked to the other end and peeked out. They were nowhere to be seen. I later learned they had gone to the side where I’d disappeared, looking for me. I went back the way I came and saw no one, so I crept towards the fron and looked out. I saw Angela’s boyfriend driving away and Kim and Angela went into Angela’s house! I was stuck!!!

I had no idea of what to do. My car keys and my house keys were in my jeans in Kim’s house. It was a long walk home from there and I felt sure I’d be seen by one of my neighbors or something. I went in back of her house and debated sitting there until Kim came home the next morning. The sky was already getting lighter. Dawn was only a few minutes away.

Despite my despair, the humiliation of my dilemna had my dick hard and throbbing. Since it kept me from concentrating on the situation at hand, I began stroking it and, moments later, was rewarded by the most intense orgasm I’d ever had in my life. Unfortunately, that was followed by the most crushing feeling of self-humiliation imaginable. Not erotic in the least, I was just plain mortified, beyond anything I’d ever felt. I wanted the earth to open up and swallow me. Before I knew it, I was crying.

As the humiliation that followed my orgasm faded a bit, I began to contemplate my predicament. After a minute or two, I decided that walking home was my best bet, since I often left my bedroom window unlatched to facilitate a quiet entrance when drunk.

As I passed Angela’s house, I could see the lights were on in one of the upstairs bedrooms. I thought I could toss some pebbles up and maybe get the girls’ attention. It would mean humiliating myself in front of Angela, but she was a sweet girl who probably wouldn’t abuse me with the knowledge the way Kim seemed to enjoy. The trouble was, Angela had two big jock brothers and they had the other upstairs bedroom. I’d been up there once or twice when I’d hung out with them, but the geography of the house was fuzzy in my mind. I finally decided that if her brother’s answered the window, I’d just have to hide. I tossed the pebbles and after about the third one, Angela opened the window and looked out. I was trying to hide behind a bush but I don’t suppose it hid much. She laughed at the sight of me and called Kim over to the window. I angrily demanded Kim come down and let me back in her house to change.

Next thing I knew they were both at the front door. Kim wouldn’t take me back until I gave Angela a good look at my feminine alter ego. Leaving her laughing and promising to wait up for Kim, we finally returned to Kim’s house.

She told me that when I ran away, she assumed I’d gone home. I told her I had no keys and that just made her laugh some more. But when she saw what I’d done to her Mother’s panties and slip, she wasn’t laughing. She stood there and made me suck my cum out of the lingerie and then she made me hand wash both items. Then she cleaned off the make-up and I got back into my clothes and went home.

A week later at the park, Angela climbed into my car and made me tell her the whole story. I told her how Kim kept upping the ante and how I’d been powerless to do anything but go along. She said that it was a trait she got from her Mother who had her Dad, a burly construction company owner, wrapped around her little finger. "Like mother like daughter," said Angela.

"She told me her side of it that night after you changed and went home. She was going to tell everyone anyway, but I made her promise not to."

"Thanks Angela."

"It’s okay. But I’d like a favor in return."

"Sure, Angela, anything I can do."

"Well, see, I couldn’t talk her out of making you dress up for Melissa. That you’re going to have to do. And I know she’s going to make it just as humiliating for you as she can. So what I want..."

"Yes?"

She gave me the cutest smile and said, "I want to be there to see it too."

 

THE END

 

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