Dressing For Melissa       by: Cissy Gaye

 

It was the early 1970’s, the height of the glam-rock era, when I let a girl named Kim dress me up in drag. The events of that evening spiraled hopelessly out of my control and I was publically humiliated by Kim, then locked out of her house still in drag. This led to her friend Angela seeing me in my ridiculous outfit, an event Angela confessed she hoped to see repeated. Kim had already promised to dress me up again to surprise and amuse her friend Melissa, who Kim knew I had a big crush on. It finally happened.

It was the middle of summer when Kim made good on her promise to dress me in drag for Melissa’s amusement. In that time, Melissa and I had begun dating. When her boyfriend broke up with her the week before her senior prom, she had asked me as a friend to fill in and I had jumped at the chance. We went out a few times after that and found we really enjoyed being with one another.

Melissa had made a remark once that it wasn’t fair that women could wear pants or skirts, while men could only wear pants. As a cross dresser, I’d been secretly thrilled to hear her express such an opinion. I was already flirting shamelessly with her, whenever her jerk-off jock boyfriend wasn’t around, and so I told her that she was right, it wasn’t fair. "I’ll make you a deal," I said. "If you and I ever get married, I’ll let you wear the tux and I’ll wear the gown." Melissa had laughed and said it was a deal. It was my mention of that conversation that had gotten Kim so revved-up about dressing me as a girl. And so, a few months after my first humiliating foray into public cross dressing, Kim told me it was time to play our little joke on Melissa.

Angela had already confided to me that Kim had every intention of making this second instance of female impersonation as humiliating for me as she possibly could, so I kinda knew what I was getting into. But this was the kind of opportunity I simply could not pass up. Besides which, I really got off on the embarrassment and I knew the other girls wouldn’t let Kim go too far. At least I hoped they wouldn’t.

So we chose a weekend when Kim’s folks were away again, and got together Friday night to transform me. This was a good time also because the guys in our crowd had taken a road trip to see a concert in Pennsylvania, so I had no worries about them seeing me. Kim conspired with Melissa’s two best friends, Jeannie and Kate, to lure Melissa to the rendezvous, a golf course in a nearby neighborhood, where we went occasionally to drink and make out. Her plan was to have me just saunter up with her, join the party and see how long it took Melissa to realize it was me. Since they ‘d be drinking wine and smoking pot, she assumed Melissa would be a little hazy by the time we got there and might take awhile to figure things out.

Friday arrived and I reported to Kim’s house for my feminization. A few minutes after I arrived, I was stripped and in the shower waiting for the Nair to do its magic so I could shower it off. I heard the doorbell ring, which I assumed marked the arrival of Angela, which was only partially true. It seemed that Angela had been unable to keep from confiding in Cindy, another girl in our crowd, who was probably my best friend among the girls. Cindy had been in stitches when she heard the plan and begged to be able to come along. Knowing how much Cindy and I liked each other, Angela had assumed it would be all right.

But the way I found this out was when all three gorgeous brunettes trooped into the bathroom together and, seeing me standing in the shower naked, burst out laughing. "I told you it was little," said Kim, pointing at my less-than-impressive cock. "You weren’t kidding!" said my "good" friend Cindy. Angela just giggled.

I was so embarrassed, but they wouldn’t leave, nor let me turn around. They wanted to look it over and, if I didn’t allow it, Kim said she’d tell everyone that I was a minnow dick. This had them in hysterics and I was then treated to every small dick joke they could think of. I stood there and let the humiliation wash over me. I finally got a boner, small enough to bring additional snorts of derision. The most embarrassing part was that these girls, by their own admission, had only seen a couple of cocks in real life and maybe a few in porn mags. If they found me woefully inadequate, what would happen when I met a woman with experience? They thought of that, too, and that caused another round of laughs.

Angela, of all people, made up a pantomime gesture of putting a magnifying glass to her eye and manipulating a pair of tweezers with her other hand. The girls loved it and that became their private signal to humiliate me. For years after, when I’d see any of them, they’d do that gesture and laugh. I always got a kiss for being a good sport about it, but they never let me forget that my tiny pecker was quite amusing to them.

Finally, Kim said to rinse off the Nair and, except for my crotch, I was hairless from the neck down.

"No beach for you this summer," pointed out Cindy, but I didn’t care. It did, however, make me realize I’d have to be careful who saw me until the hair grew back. Angela said that my skin would need moisturizers applied to prevent it from being damaged by the Nair’s harsh chemicals. So, three beautiful girls rubbed every inch of my body with a sweet smelling lotion. It was heavenly. Then, they worked on my hair. Since it was shoulder length they just trimmed some at the front to make bangs, then gathered the rest in a ponytail which they tied off with a rubber band and a little black chiffon scarf. Kim added the earrings from the last time - clip-ons with annoying little bells that rang in my ears whenever I moved.

Next Kim presented me with the same yellow rhumba panties I’d worn before. Once I had them on, with much laughter from the girls about how my poor little penis tented out the front of them, Kim handed me the same frilly green negligee from our earlier adventure and then my makeup was done. This was hard, as each girl wanted a hand in it. When they finished, I was glad I didn’t look as slutty as when Kim had done it alone.

Next,off with the negligee and on with the bra and the garter belt and stockings. They filled the bra with panties from the hamper. Rolling the stockings over my newly shaved legs was an incredible experience and my cock was throbbing from the excitement. When they added a short, lace trimmed red slip, it was all I could do not to swoon as the silky garment floated down over my shoulders. Cindy pointed out the way my erection ruined the line of the slip and Kim said, "Yes, we had this problem the last time. I guess we’ll have to solve it the same way." Since no one asked what that meant, it was clear they’d planned on this. Kim spread out beach towels on the living room floor and had me lie in the middle. I didn’t argue.

The girls surrounded me and I was handed a pair of panties. I lifted the slip and pulled down the panties I was wearing - quite a problem with the garter straps over them - and began to jerk off. The girls kept up a running commentary about how silly I looked and how tiny my dick was and how girlish I looked in a slip. It took about five minutes before I shot an incredible quantity of jism all over my belly. The girls all cheered, but I felt a total fool now, since cumming ended my erotic enjoyment of my predicament. But I knew there was no getting out of this. And I had a good idea of what was coming next.

"Now," said Kim, "this is the really fun part!" And I could see from the looks of anticipation and glee on the girls’ faces, that they knew exactly what was going to happen next. Kim scooped some of my seed up onto her finger and, as the girls began giggling, brought it up to my mouth. She didn’t say a word, just gave me a look. I opened my mouth. As she put her finger inside and I licked my sperm off her fingertip, the girls broke out in hysterical laughter, punctuated by jeers. Angela, sweet, gentle Angela, looked me right in the eye and said, "Wow, you really are queer, aren’t you?" I hung my head as the girls howled.

They took turns feeding me my seed. When I’d finished it, it was time to tuck my "little guy" away and put on my outfit for the evening. "Okay, Angela," said Kim, "let’s see what you’ve got."

Angela brought out a bag and took a dress from it. She explained it was one of her sister’s dresses. Marianne, her sister, was several years older than we were and was a big girl. Not heavy, just tall and big-boned. It was agreed that I should have no problem fitting into her dress. It was a style popular for a short time in the early to mid 70’s, one which I’ve never seen since, although I’m always looking. It was an extremely short dress made of silky nylon jersey. The skirt flared out and ended in a little ruffle. Barely concealed below the scandalously short skirt was a pair of silky panties that matched the pattern of the dress, which was black with a spray of yellow flowers across it. The neckline was a simple scoop design. The sleeves were long and they ended in big floppy, femmy ruffles. The ruffles were the same fabric as the dress on the outside, but inside the ruffle, there was a change to a fabric in a solid color, in this case the same shade of yellow as the flowers on the dress. Each of these girls had a similar dress in their wardrobes and I’d spent many a day at school salivating over the intensely erotic vision of these gorgeous girls in these flirty, girlishly sweet, yet sexy dresses. I couldn’t believe I was actually going to get to wear one.

Th girls established that a red slip wasn’t the right look, so they adjourned to Kim’s mother’s bedroom to look for an alternative. I tried a half dozen different slips before Kim found a pale yellow shorty that would probably fit under the dress. Then I was permitted to don the beautiful garment. It fit beautifully and the slip was almost short enough, but a hint of the lace hem remained visible under the skirt. "Good enough," Kim decided. Giggling at my humiliation, the girls agreed it would have to do. I put on the same ill-fitting sandals I had worn previously and struggled to walk.

They took another fifteen minutes to make me practice my girly walk and gestures. Kim handed me a purse with my keys and wallet in it, plus some makeup. She showed me the keys and said, "In case we lose you somewhere I want you to be able to get in your house." The girls laughed at my reaction to the idea they might "lose" me and comforted me with hugs and little sisterly kisses.

We went outside and stood in front of Kim’s house, waiting for her to lock up and join us. The gentle breeze was even more intoxicating this time as my skirt barely covered my pantied ass and the stocking tops became a center for tactile sensation. I think I moaned a little in delight, as I smoothed my skirt down. Cindy said, "You really are enjoying yourself, aren’t you?" Angela was waiting for my answer, too, but I decided, at this point, I had very little to lose so I told the truth. "Yes, this is the most erotic thing in the world to me. I can’t describe it. I can’t believe I’m telling you this. Please keep this a secret," I pleaded. They both promised it was our secret and I got more hugs and kisses.

We got into Kim’s car and headed for the golf course. It was nearly 11, the time they’d arranged to meet Melissa, Jeannie and Kate. "They’re probably pretty high by now," Kim said. The ride was pretty uneventful. I was scared we’d get a carload of guys beside us at a light and I was worried what cruelty that might inpire in Kim, but no one paid us the slightest attention. Kim noted we needed gas, but since it was getting late, she decided to put off getting it until after our "party".

There was an old access road for the power company that ran along the edge of the golf course. On the other side of it was an embankment with homes on the top. It was an easy place to hide the car and enter the back of the golf course. Since we were the only ones who had found it, so far, it was a really nice place to have a little "wine and smoke" party. By the end of that summer, word had gotten around and there were too many people gathering and, with that, the cops shut it down and the power company put up a locked gate. But for a little while, we had our own private hideaway.

Kim parked next to Kate’s car and we headed in through the woods, following the path we always used. It was a lot harder to navigate in the high heels. The other girls had dressed up a little, too, so I wouldn’t stand out as much, but they still had jeans or shorts on. I was the only one in a skirt. We were just about at the end of the trail when Angela said, "Wait a minute. What are we going to call you? You need a girl’s name or the secret will be out before we start."

"Have any personal choice?" asked Cindy. I wanted to say Cissy, since that was what I called myself in my own mind, but I didn’t want to admit that to Kim. They tried and discarded a couple of names before Angela said, "How about Trish?" They mulled it over for a few minutes and I nodded my approval and that was it - I was Trish. "I’ll say she’s my cousin from Connecticut, down for a visit," said Cindy. "That’ll explain why she’s so dressed up."

We found Melissa, Jeannie and Kate sitting on blankets next to a sand trap by the 12^th hole’s green. It was the area we generally hung out at. The girls were all really drunk and stoned and it appeared that Melissa barely gave me a glance. Jeannie and Kate, however, being in on the joke, were trying to get a good look at me, but it was too dark to make much out. Melissa was a brunette, with a great figure and a very pretty face. Kate was a redhead and Jeannie was a dirty blonde. Kate was really cute. Jeannie was kind of plain looking but very sweet. I was gently manuevered into sitting next to Melissa, which I did as gracefully as possible, kneeling first then sitting sideways with my legs tucked under me and off to the side. I smoothed my skirt as Cindy introduced me. Melissa said hello and passed me the joint in her hand. I took a hit and passed it to Kate, who was looking at me now in amazement. I gave her a look and she recovered her composure.

After a few minutes of smoking and drinking the cheap, sweet wine they had, the conversation turned to boys. Kim said that her boyfriend was getting on her nerves and she was thinking of dumping him. Then she asked Melissa, "So, how are things with Gordon?" I couldn’t believe she was bringing me up like that. I was terrified, yet I couldn’t deny I was dying to hear what Melissa would say about me in my "supposed" absence.

"Gordon is really sweet," said Melissa in that voice that lets you know there’s a but coming. And it came.

"But I’m doubt it’s going to last."

"Why not?" asked Cindy. "I thought you two were really sweet on each other."

"We are," said Melissa, "but..."

"What?" the girls demanded.

"Promise you will never say a word about what I’m going to tell you," commanded Melissa.

The girls all agreed. I just shrugged. I was from out of town, supposedly, so it didn’t matter if I promised.

"The thing is," Melissa said, " is that Gordon’s not really...shit, how do I say this.... he’s not...damn it...I really love him but his dick is so tiny."

The girls burst out in laughter. I was mortified, but I had to giggle along.

"I mean, I jerked him off once and there wasn’t enough to wrap my whole hand around!" Melissa continued. "I had to use the tops of my fingers." The girls were rolling now. "And I really wanted him to be the first guy I fuck, but what if I do and he’s not big enough for me to feel? I mean, I wouldn’t hurt his feelings for the world, but, the bottom line is, as a man, he just doesn’t measure up."

The shame and humiliation burst forth like my skin was on fire. As humiliated as I’d felt at earlier points in the evening’s events, it was nothing to compare with having my manhood discussed so openly and cruelly in front of these girls by a girl I was in love with. And for them to know I was sitting here, in drag, hearing this, just made it all the more hilarious to them and painful to me. I could feel tears welling up in my eyes.

"But that’s not the worst of it," said Melissa. "I made a remark once about guys should be able to wear skirts and he said if we got married, he’d wear the wedding dress and I could wear the tux. Can you believe that? I mean what kind of a queer would say something like that?"

Jeannie was nearly choking now. Kate had tears of mirth running down her face. Cindy gave me a look of compassion that gave way to a grin and Angela was shaking like a leaf from the laughter. Kim just sat there giggling and looking at me with the meanest expression, enjoying every second of my ridicule, drinking in my utter degradation like it was the wine of life. That’s when I knew that Kim really was a bitch on wheels and that I would be hearing about this forever.

"So what are you going to do?" said Kim.

"Well, I should at least get him to put on a dress for me, so I can see how ridiculous he looks. Then maybe talk him into going out somewhere with me in the dress. Then, when I’ve got him out away from home somewhere, I’ll tell him I want a real man and leave him there. Let him figure out how to get home on his own."

The girls all agreed with much laughter that Melissa’s idea was suitable punishment for a faggot queer. Then Melissa turned to me and said, "What do you think, Trish?"

I couldn’t bring myself to speak. I could feel the tears running from my eyes. I looked into Melissa’s eyes and gently shook my head.

"Or should I say, Gordon?" she said laughing and the girls all broke down in another fit of hysterics. My jaw dropped.

"Gotcha!" said Melissa. "Gotcha!" said Kim. "The look on your face," Cindy managed between laughs. Jeannie and Kate were literally rolling around in tears of hilarity. Angela leaned over and patted me on the knee reassurringly and said, "The joke is on you, babydoll."

I was in total shock. It took about ten minutes to calm them all down. Just when they’d settle, one of them would start to giggle and the whole bunch would be laughing again. Melissa leaned over and pushed me over on my back. Then she started kissing me with a vengeance. "C’mere, girl," she said and she started running her hands all over me, feeling up my "tits" and rubbing my crotch. It was paradise. The girls kept teasing me about how I’d fallen into their trap and gradually I got the whole story. Kim had told Melissa about dressing me up the day after the first time and between them, they’d concocted this plan. Dating Melissa had just sort of happened before they were able to put the plan into effect, but Melissa gave in to Kim’s repeated pleas not to abandon the joke. Because she sensed I would enjoy the experience in the end, Melissa agreed, but they assured me they were all sworn to silence. These six girls were the only ones who knew and were the only ones who would ever know. And I got some very nice kisses along with their promises. So nice that Melissa growled at Kate when she didn’t come up for air soon enough.

"Sorry," Kate said. "I just liked the taste of his lipstick." That brought another round of laughter and I wondered how these girls’ boyfriends were going to be begged and wheedled and coerced to try on a bra or let their girl put makeup on them and so on. Several years later, Kate told me she’d finally convinced one of her boyfriends to let her dress him up. She said they had great sex that night.

"C’mon," said Melissa, dragging me to my feet. "I want some privacy so I can have my way with you." She grabbed one of the blankets and one of the bottles of wine. Kim looked at her watch and said, "Twenty five to twelve. How about we leave at 12:30 and go back to my house?"

Melissa checked her watch and said okay. She took me out into the middle of the fairway about 50 yards from where the rest of the girls were. She looked around for a minute before choosing a spot for our blanket. Then we laid down and started to make out. She told me that she thought I looked cute in Angela’s sister’s dress. She fingered the barely visible lace of the slip. "That’s a nice touch," she said with a grin. She reached into my panties and started to stroke my dick and I guess she saw the look on my face. "Did I upset you with those things I said?" she asked.

"Well, I know that to make the joke work, you had to say something that would really humiliate me, but it does make me wonder how you can want to be with me," I said. "I mean, if I’m that unsatisfying."

"Look, Gordon, or should I stick with Trish for tonight?"

I shrugged.

"You do have a small cock. All those girls knew it from when Kim told us about your first dress up adventure. And she told us how much it embarrassed you. So, it was the natural thing to say to humiliate you back there. I don’t care about the size of your cock. You’re the first guy I’m going to sleep with, so it’s probably better to start with someone small. And let’s face it, as much as we tease about it, we’re not going to get married. This is a summer fling. We’re both going away to college in September. You didn’t expect this to last past then, did you?"

"No," I said. "I knew that couldn’t work."

"Look, us going out kind of happened by accident. I like you too much as a friend to want us to get all possessive and stupid about this. Cause then when we have a fight and break up, we won’t be friends anymore. I was hoping this could just be a really nice time for the summer and then we could still be really close instead of hating each other the way other couples always end up."

I agreed that she was right. I loved her, but I had never thought it would last. She attracted too much attention from big jock types. I knew we ended up together as a fluke and I was grateful for the good time we were having. And the better time we were going to have, if I could believe what she was saying about me being the first she would fuck.

She went at me again and pulled down the panties and stroked my cock. "Tell me the truth, Trish," she said. "You really enjoy all this, don’t you?"

I confessed all at that point and I told her that I had thought I would have to admit all this eventually and that I’d expected that to end our relationship. "So," she said, "this is working out better than you expected, right?" I had to agree. She promised that she would explore my fantasies with me and before I knew it, she was sucking my dick and I came like a banshee into her mouth. She came back up to my face and opened her mouth a little. I could see my jism on her tongue.

"Rumor has it..." she said, but it came out more slurred than that. I just nodded and opened my mouth and we kissed and passed my sperm back and forth with our tongues.

"This is kinda interesting for all of us," Melissa said when we came up for air. "We get to see you do things and we can ask you stuff. I know it’s weird, but we all decided that we like this about you. It’s like we all have a secret friend who lets us see his cock and watch him jerk off and lets us talk about stuff, you know, kinky stuff. And, I have to admit, it’s kinda fun to know we can pull embarrassing tricks on you and you won’t get all pissed off at us. Let’s us take out some of our frustrations with men. You don’t mind if we do that, do you? Use you to get even with, when men piss us off?"

"No, of course not, you know I like it. Just as long as nobody else finds out. And I like feeling like I’m almost one of the girls."

"Well, you are in a way. And no one will tell. Kim is the only one who’s not to be trusted, but she knows I can and will beat the shit out of her if she does anything to hurt you. Wait’ll you hear what we really talk about when it’s just us girls."

"I think I got a little taste of that before," I said with a rueful smile. "I have to admit I’ve never been so humiliated in my life."

"And you loved it, right?"

"Uh-huh."

"Well, the night is young, sweetheart, and for all you know, we might have more surprises for you." With that, she stood up before I could ask what those surprises might be, checked her watch and said. "Almost midnight. I’m gonna go get another joint for us. Wait right here, girly."

So I lay back and wondered what else they had in mind for tonight. I’d already assumed that putting gas in Kim’s car was going to be my job. I wondered if that was what Melissa had meant. She was gone for awhile and I sat up to see where she’d gone. I couldn’t see the other girls on their blanket anymore, so I stood up and suddenly felt myself get hit with a spray of water. Then the water started hitting me from all directions. The golf course sprinklers had come on. I grabbed the blanket and the bottle of wine and tried to run back to where the girls had been, but I got there and they were gone.

"Oh shit!" I thought. "They wouldn’t leave me here, would they?"

I made it to the path in the woods, but by that time I was soaked. As I stepped out from the trail, I saw both cars, filled with girls watching me. They laughed and jeered at me. "You have to dry out before you can get in my car," said Kim. "Why don’t you walk to the street and we’ll wait for you there." And with that they took off.

It was about a quarter of a mile, I guess, and my feet were sore by the time I got to the end of the access road, but they were there, like they’d said. I got in the back seat of Kim’s car with Angela and Melissa. "Enjoy your shower?" Melissa said with a nasty little grin.

"You mean you knew..."

"Sure, the sprinklers come on at midnight. You are so easy to set up, honey. We’re gonna have a lot of fun with you, I can see."

Sure enough, the first thing Kim did was stop at a self serve gas station. She turned to me and said, "Trish, honey, be a good girl and put five dollars worth in for me please?"

I got out, feeling totally ridiculous under the bright lights of the station. I pumped the gas, looking around constantly, fearing who might pull up. Kim wanted me to go into the office to pay, but Melissa took the money from her and did it, saying, "Enough’s enough."

We went back to Kim’s house and started drinking in her parents rec room in the basement. We played strip poker and, even though I wound up losing everything but my stockings and garter belt, and I had to endure another round of tiny pecker jokes, I did get to see most of the girls topless and even Kate bottomless. She was the worst poker player I’ve ever seen.

Then they started making me try on Kim’s mother’s clothes. I had to model the outfit I’d worn the first time Kim dressed me up, and then a few others. Finally, they demanded I jerk off for them. I tried to get out of it, since I’d already cum twice, but they were really insistent, so I laid down on the floor with all of them sitting around me in armchairs and on barstools, still in their underwear. It took a long time for me to cum this time and they had a lot of fun teasing and humiliating me. Then, we went upstairs and Melissa and I were given the use of the master bedroom as the girls curled up in Kim’s room and on the couches in the living room.

Melissa said, "I guess after all that I’m not going to get laid tonight, am I?"

"Sorry," I said, struggling to keep a straight face. "I don’t think I’m up for that."

She laughed and curled up in my arms and we fell asleep.

The next morning, she said, "I think you should fix the breakfast and serve us in your little dress, don’t you?"

So, she helped me take off the previous night’s makeup and replaced it with a little from her purse. Then I put my outfit on and went out to the kitchen to make breakfast. The girls were all delighted that I was going to serve them and they had a lot of fun making me run around getting them whatever they wanted. When breakfast was over, Melissa pulled me back into the bedroom and said, "Now, did that get you horny enough to fuck?"

"Yes, dear." Amazingly enough, I was just big enough to make Melissa happy for her first time.

Well, that’s it. I lost my virginity and then I stayed in a dress the rest of the day. We all just hung out and got drunk and stoned again and they humiliated me by making me do little tasks and such. I ended up dressing in drag in front of these girls about a half dozen times all together and whenever Melissa and I were alone together, she’d have me put something on. Our little romance lasted until she went away to college in the fall, but I changed my mind and stayed local. Melissa had introduced me to her neighbor, Janet, who was several years older than us. Janet was a really kinky woman, the first one I met who actually liked what I liked before I even brought it up. And we had a lot of fun together. But that’s another story.

THE END

 

 

© 2000
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.