Chapter 23 — Greg's First Date

 

My skimpy shorts and top offered little protection against the later afternoon breeze as I quickly walked the distance home. The awkwardness of the heels and heavy hoops were an additional burden and fought the wave of tears that struggled to overcome me. Was I really looking forward to getting home, going to the bathroom and getting out of this skimpy outfit! When I came through the back door, however, Mom was waiting and she started on me even before I had my sandals off.

"Where did you get the little statue? What happened, sweetie … did you win an award or something?" She fingered the top of the trophy I'd won at school. I hadn't noticed before, but it was topped with a likeness of a man being chased by a woman: Sadie Hawkins going after her husband. I remember staring at the ridiculous image before me and thinking, Oh, that's just great! Mom looked from the trophy to me and back again, her face beaming with delight. I felt my blood pressure go up as I realized what was probably going through her mind. " It looks like you had fun today. Come on, have a seat and tell me all about it!"

The questions were fast and furious and for the first time in my life I had to take charge of the situation. "Mom, please! My feet are absolutely killing me," I complained loudly. "They’ve been cramping ever since lunch. Let me get them off and then after I go to the bathroom I’ll tell you about all about everything."

Thank god, she at least let me take off the shoes and go to the toilet. I thought I'd never stop peeing! When I finally came back I stretched out on the couch and removed the heavy hoops, again with the gawky awkwardness that comes from inexperience. Then I started to take down my hair as I recounted the events of the day, from the bullying and teasing all through how I had been asked out on a date for the dance that night by Kathy.

Mom relished every word I said about the day's events, drinking them in with a thirst that made me uncomfortable. Especially when it came to hearing about my difficulties. She seemed more interested than concerned when she heard about my encounters with Todd and Joe, for example. After making me tell the story at least twice to make sure I hadn't left anything out, she questioned me forever on the details, holding me by the hand and squeezing it tightly as I searched my memory for the answers she wanted. When I made the mistake of telling her how Joe had tried undoing my shorts, her eyes lit up and she pressed on. "He had his hand down your pants? Good grief, girl, how far? He didn't get them off, did he?"

I couldn't believe she was asking me that. "No, Mom, he didn't get them off!!! Please … that's nasty!"

My mother gave me a funny look. "This Todd boy … he sounds like he's obsessed with you. He didn't try to kiss you, did he? You didn't let him, did you?"

A guy … trying to kiss me! I didn't know what to say to that one. "Eww, Mom!!! Don't be gross! That's sick!" I couldn't believe how she was acting. Sometimes she goes too far, I thought to myself.

"Things happen," she said cryptically. "You'd be surprised."

When Mom was done she warned me about hanging out with the wrong crowd.

"Now you see what girls have to go through? Just because someone dresses nice people think they can be harassed and touched in places they don't like. It's not fun, is it? Some of those boys can really cause you a lot of trouble, sweetie, so you'd best be on your guard. Next time do yourself a favor. Try and find a nice boy you can trust."

I didn't like the sound of that. "What next time?" I wondered. "What nice boy?" To be honest, I was too afraid to ask.

After smiling through my recounting of all the teasing and abuse I suffered, Mom asked me how I felt about the way I was treated. I told her how much I hated it, and I ended up sobbing as I realized none of my friends would ever look at me the same again.

Mom was beside herself with joy when I told her about the awards ceremony and I had to tell that story at least four times! "It's too bad I wasn't there with my camera," she said wistfully. "I'd love to have a picture of you accepting your little trophy. Maybe I'll call the school and see if anyone shot any film."

The trophy ended up on the mantle, of course, where it was eventually joined by a framed snapshot of me onstage with the principal accepting my award; Mom got that from the school paper, which ran the photo three times that year in various issues about school events and activities. Another shot of me posing with one of the other crossdressed boys — remember the sophomore in the country dress? — was included in our yearbook. I winced at the thought of my photo being in the hands of every high school boy in our county.

Anyway, my mother was also delighted to hear that I'd met a girl and that I had accepted her invitation to attend the school dance. She said she would be happy to drive and pick us up, saying that going to the dance would be the perfect conclusion to such a special day.

"I've got the perfect outfit for ‘Pamela’ to wear, too, sweetie. Your little Kathy is just going to love you when she sees it!"

Sighing helplessly, I called Kathy and told her my mother could drive and got directions. We’d pick her up at 7:30 sharp.

I got out of my shorts and top, but left on my bra and panty girdle as Mom had instructed. She handed me a short white satin robe to wear, which enhanced the female image I projected with my full bust. I creamed off my makeup and went into the family room where I flopped down in front of the TV and then dozed off for a nap.

When I awoke I had slept almost two hours and it was time to help Mom with dinner. At least I didn’t have to don my hated apron as all I had to do was set the table and pour drinks. Those damn nails were still getting in the way as I pulled napkins out and folded them next to the silverware. "God, I can’t wait to be freed from these stupid fingernails," I thought. They were every bit as restrictive as the heels and girdle, in some ways even more so.

When dinner was over, it was time to get ready for the dance. Mom had me shower, again wearing a plastic shower bonnet to keep my hair dry. I got out and went back into my bedroom to find an fresh outfit laid out, this time a red silken mini-dress with a flared, flirty skirt. There was also a fresh padded bra, a shorty panty girdle and a pair of sheer nude stockings waiting for me. I dressed myself as usual, still a little clumsy with the bra hooks and long nails, but left off my shoes until the last minute. Mom insisted that I wear my gaudy red high-heeled sandals, saying that they’d go perfectly with my new dress and hose. I made a case for wearing other shoes, but she wouldn’t hear of it.

"Not another word, unless you want to wear them to school every day next week."

That shut me up.

The dress was awful snug, except for the flared skirt. I asked Mom if it was a good idea for me to wear something so revealing. My question served mostly to irritate her. "You have something you’d rather be wearing?"

"Yes, ma’am. I mean, no, ma’am. I … I just think … doesn’t this dress let people see my underthings? It’s so tight." I plucked at the material in an attempt to get it to fluff up a bit and not cling so tightly to my body. "My … bra… it sticks out too much …."

Mom smacked my hands away. "Stop that! See, you silly girl, that’s how it's supposed to work. Girls wear pretty underthings so they can show them off. This dress is perfect for that. It's so thin, so clingy, it really shows off your curves, too. See?" To my horror, she ran her hands over my padded bra, emphasizing the budding breasts beneath.

"Consider yourself lucky. Some girls your age don't have any boobs at all. You look just perfect!"

 

 

"But … I'm not a girl," I said unconvincingly ….

I did most of my makeup, except for the eyeliner, which I had never painted on myself up to that point. Mom fixed my hair up, this time with dual ponytails out to the sides. My stomach sunk when I saw how childish the little red scrunchies looked with my bangs and I wondered what Kathy would think. My mother then used a brush to accentuate my cheeks with some blush and I was almost ready to go. There was the mandatory perfume which I got to apply myself this time, with reminders to get behind both my ears and on my wrists. I thought I’d perhaps escaped the heavy hoops, but she produced them at the last minute and fastened them to my ears. I also ended up with the bangles decorating my wrists, another burden to bear. She handed me one of her nicer wool sweaters and I got my purse and out the door we went.

Kathy lived about ten minutes away and we were there in no time. Mom stayed in the car as I minced up the walkway to the front door. I rang the bell and Kathy answered, dressed in boy clothes of a t-shirt, denim jeans and Keds. Her hair was slicked back into boyish style and there was a swagger to her step that made me feel funny.

"Hello, ‘Pammy,’" she said gleefully. "I love your hair! And that dress … wow! Cute figure. You really look cool! Just like a girl!"

She invited me inside and her parents were both waiting in the living room. It flashed through my head about how you never get a second chance to make a first impression. I was thinking, What will they think of me when I come back for a date dressed as a guy, instead of in this prissy costume?

Mr. Wade was a large man in both height and girth. He shook my hand with a "Hello, Greg." and returned to sit where he was reading the paper. Guess he wasn’t in the mood for conversation or maybe he was just at a loss for words.

Mrs. Wade was just the opposite. She smiled as she took my hand and greeted me with affectionate "Oh, Gregory, or is it ‘Pamela?’ I swear to goodness, you look even prettier than Kat had describe. Oh, look at those cute little pony tails. They’re absolutely adorable! I’m so please you agreed to go to the dance with her." She hadn’t let go of my hand and instead escorted me toward the hallway where a boy younger than myself was standing quietly.

"Come here, Stephen," she ordered. It was a definite command and not a request. The boy sheepishly approached as she introduced him as to me, telling me that he was two years younger than Kathy and was in the sixth grade.

I took his hand to shake it and said in a friendly voice, "Hi, Steve. It’s nice to meet you." He looked at my hand and my painted nails, but he never made eye contact with me. He quickly withdrew his hand once I had released it, backing away into the doorway.

"Doesn’t Gregory look nice all dressed up as ‘Pamela?’" Mrs. Wade asked him. She turned to me and explained how Stephen didn’t think that boys could be made to look as pretty as girls. "I’ve told him that with the right clothes and makeup, that young boys could be made to look exactly like teenage girls, but he wouldn’t believe me."

At this point I was wondering why she would be having this conversation with him in the first place. Had it come up when Kathy had told him about Sadie Hawkins Day, or was something darker smoldering beneath the surface?

"Now do you believe me?" She turned her comments back to the younger brother. "You see how easy it could be done?" The tone more threatening than informational. "I want you to take a long look and remember what we talked about," she continued.

His first and only words were a hushed "Yes, Mom," delivered with his eyes glued to the floor near our feet. At first I thought he might be staring at my heels and painted toenails, but then I realized it was a posture of submission. Yes, there was certainly something unspoken going on and I could only surmise what it was. Maybe I could get Kathy to fill me in once we were alone.

The conversation eventually returned to Kathy and me. "You kids have a good time. Kathy, you’re to be home by midnight even if Greg’s mother is driving," and so on. Kathy picked up a boy’s varsity coat she’d borrowed and we headed out the door to where Mom was waiting.

Before we could get in the car my mom made a big deal out of taking our picture together. "Oh, you two, you look so sweet together … a handsome young boy and his beautiful girlfriend … I’ve just got to get this on film. Here, I’ve got my camera ready, it’ll take just a second!"

Not feeling dressed appropriately for the occasion, I tried to get out of it. I made up some excuse about being late for the dance; to my surprise, Kathy was as enthusiastic as Mom was, saying it would be fun to have a photo of the two of us on our first date. I felt so stupid as she pulled me over to my mom’s car and put her arm around my waist and pulled me close. All I could do was grin like a fool while the little flash went off over and over again.

Once we were done I opened the front door thinking we could both squeeze in, but Mom suggested that we sit in the back together. Kathy opened the door for me and taking my hand offered to assist me since I was wearing more restrictive clothing than she was. When we were both buckled in, we headed for the school as the dance was going to be held in the gym.

"By the way, Mom, this is Kathy. Kathy, Mom," I said as my way of introduction.

"It was so nice of you to ask Greg to the dance," Mom said, her face beaming with delight as she saw just how pretty my date was behind her boyish disguise.

Kathy beamed right back. "Well, when I saw him get on the bus this morning, I just couldn’t believe how pretty he was. I knew right then that if he’d go, we’d have a great time tonight." She giggled and snuggled closer to me. She’d put her arm around my back the way boys do to girls and gave me a hug. As she talked to my mother about how it was so neat to see boys willing appear feminine, she was working her hand up under the sweater on my back. Then she started to play with my straps through the thin material of my dress and just before we got to the school, she gave the main one a sharp snap.

She pulled my head close to her and whispered in my ear, "So how does it feel to have a girl snap your bra, sweetheart?" and with that she broke out in a little laugh. "I’ve always wanted to do that to a boy whenever one of them did it to me. I love the way you blushed when I did it. You know, I think we could have a lot of fun like this." Her voice was soaking with a mischievous tone while she toyed with the contours beneath my dress.

Kathy was right, I was blushing, and my heart was pounding so loudly my ears hurt; I was surprised that the car windows weren’t steamed up, I was so excited. Needless to say, I was also struggling to deal with a growing erection; being so close to a girl and having her touch me with such familiarity, such possessiveness, well, it was extremely arousing. Just the touch of Kathy’s fingers up and down the small of my back caused me to squirm in my panty girdle. I remember wishing the car ride would end soon, I was so uncomfortable.

Mom dropped us off at the bus turn-around and we walked the distance to the gym, the echo of my heels bouncing off the vacant walls of the hallway while her Keds were mute. When we arrived at the gym, we were both required removed our shoes to keep from scuffing the hardwood floor. An area along the west wall had been set aside for stacking them and we left them there next to each other.

I was overjoyed at getting out of my heels as the pains had returned much quicker this evening. I just wished my stockings did a better job hiding the bright color on my toenails. No matter. Kathy seemed to like them, which was all that mattered, I suppose.

We eventually found a group of Kathy’s friends and joined them next to the dance area. We chatted about the way different people were dressed and her friends were complimentary to me as well. I had a little trouble managing my dress, purse and bangles all at the same time, and Kathy was quick to give me pointers in how to act. I felt kind of silly, posing and posturing like a girl in my feminine disguise, but the more I did it the more my date seemed enamored with me. I finally just took a deep breath, and mentally jumped into my role as the "girl" of our twosome. What the hell … I may as well, I thought as Kathy gave me an affectionate wink and snapped my bra strap for about the hundredth time that evening.

I wasn't the only boy in feminine clothes that evening, thank god, but I was probably the most passable. The sophomore in the cute country style dress hadn't shown up, and I wondered if maybe his mother kept him at home doing housework in dresses on Friday nights. Nah, I ruefully decided, there couldn't be two moms as crazy as mine! Most likely he just didn't know any girls who thought he looked good in gingham.

Most of the other guys in drag were the jocks in their mocking sackcloth dresses and garish makeup. A couple wore jeans and girls' tops as part of their costumes. Their dates wore boys' clothes, jeans, varsity jackets and leather jackets and such. Several girls wore outfits similar to what I'd worn at school. The rest wore outfits similar to what I was wearing at the time. It only hit me right then and there that I was the only boy who was dressed in "normal" clothes.

Mom had done it to me again … and it was up to me to deal with my awkward situation.

 

Chapter 24 — A Night of Surprises

 

I didn't see Todd and Joe until late in the evening. They made the rounds in their crowd and kept away from the little group that I was in. That didn't keep them from spotting me, though. I felt the blood rush to my face as Kathy led me out onto the dance floor for the umpteenth time that night; with those two watching me muddle through my dance routine I was torn between clinging to the girl of my dreams and running for my life!

After a while the two bullies disappeared and I relaxed … a little. I was determined not to let my fears ruin the fun time I was having with my new friend, but it was kind of hard considering the vulnerable position I'd found myself in.

All in all I considered the night a definite success. We danced both to upbeat and slower music, and during the slow dances I got to hold her close; well, I should say she got to hold me! To my surprise my date insisted on leading and had me place my hand left on her shoulder which I quickly learned was not a control position. With her arm around the small of my back she was the one who was squeezing us together as well as controlling the direction of the steps I took. I seemed to spend a lot more time moving backwards, which kept me off guard.

With us both in our stocking feet I realized for the first time that Kathy was actually a little taller than me. I had been either wearing my heels or sitting down each of the earlier times we had been together and had mistakenly judged her to be shorter. There wasn’t more than an inch or two difference, but I had to look up when gazing into her eyes. After the third or fourth slow dance, she pulled my head toward her shoulder and had me rest it there. I didn’t realize it at the time, but later I saw the red stains where my lips had come into contact with her white shirt. When I called it to her attention, she just smiled and said not to worry about it as it was one of her brother’s shirts. She said she thought it was kind of cute.

We talked amongst ourselves during the slower dances and it was then that I asked about Stephen and the earlier conversation. It seemed she suspected him of going through her diary and had brought it to their mother’s attention. He had been warned, but she was still finding it placed in a slightly different position in her bureau drawer. One of the threats that her mother had used was to dress him in the clothes from the drawer in question if the mischief didn’t come to an abrupt halt. Kathy had further threatened to report him to their mother without cause when they had gotten into an argument over which TV program they were watching one evening. No, it wasn’t fair, but then little brothers needed to be controlled.

"He’s such a little swish anyway, it’d serve him right to get taken down a few notches," she said with a giggle. "When we were younger he loved pulling my pigtails and when we got older he loved to tease me when I started wearing bras, saying I wasn’t big enough. Well, I might just get to see the tables turned on that little brat. I’d just love to see him trying to put on a bra!"

To hear my date talking like that sent chills through my body. "You’d make your own brother dress up like a girl? Really?"

Kathy gave me a wicked grin. "Oh, in a heartbeat! He knows I can do it, too. All it’ll take is a word to my mom. What’s better, he’s seen just how girlish he could be made to look … thanks to you, sweetheart."

It seemed that "sweetheart" was becoming her favorite pet name for me.

As I mentioned, I considered the dance a positive experience in that no one picked on me and most of Kathy’s friends treated me kindly. I liked to dance, the music fit my taste, and I was having fun. Yes, all in all, it was a good night.

With all the excitement going on I forgot myself and drank too many soft drinks. That put me in an awkward predicament; I hated going to the bathroom in girls' clothes out in public as it was always such a complicated process. Between choosing which facilities and then dealing with all the accoutrements under my dress, it just wasn't worth the trouble. In this case, however, I really had to go. And so go I went. Somehow I managed to sneak away unnoticed from the gang and make my way to a deserted part of the school where I slipped into an unused boys' restroom. It wouldn't do for me to be seen in the girls' restroom; the last boy caught sneaking around like that had gotten expelled, and the last thing I needed was more trouble from my mom. The problem was that I didn't want to be seen in one of the boys' bathrooms, either, which was why I went to the darker part of the school!

I was so full of soda pop that I'd thought I'd explode before I got my dress up around my waist and my girdle down about my knees. Nervous and worried that I'd get caught, I managed to do my duty and get somewhat situated without any unwelcome interruptions.

Thank God! I thought to myself. Kathy would have loved following me right into the stall. I could hear her laughing at the sight of me struggling with my girdle and hose. I'm just not ready for that!

After checking myself out in the mirror and touching up my makeup, I innocently skipped out of the bathroom and back toward the sound of the music and laughter. For once I felt really good about myself; the way the night was going, this was going to be more fun than I could have ever imagined. I remember looking down at my red high heels and grinning because of how silly they looked on my nylon-covered feet.

"I can't believe this is happening to me," I thought. "A boy my age wearing these shoes ... and hose ... AND this dumb dress! Dang ... this is nuts!!! I wonder what Kathy and her friends really think of me?" I paused long enough to pull my dress down around my knees. "They're probably laughing at me right now. Gee, thanks a lot, Mom. How come it's always me?!"

The next thing I knew I was passing by a dark doorway and — WHAM!!! — something hit me solid in the abdomen, knocking me breathless. I wasn't sure what had happened. All I knew was that I couldn't breathe, that I was suffocating, and that I couldn't see. My eyes full of stars, I tried to get away, but a hand shoved against my chest, slamming me back, this time against the steel lockers lining the hallway. It was then that I heard a voice so dreadful that I nearly wet myself.

"Look, Joe, it's our favorite little fairy. Can you believe this? Check out his little dress. And that fruity hair. Damn, man, what a total queer!"

I couldn't believe what I was hearing. Oh, no ... not this! Not tonight ... please, God, not now ....

Yep, it was true, all right. It was my nemesis, Todd, along with his humongous sidekick, Joe. This wasn't good. Todd was cracking his knuckles while Joe finished up a cigarette. For an instant I thought about how silly they were; I mean, they weren't much older than me and here they were, trying to look so tough. Then I thought about how I probably looked to them. I looked anything but tough. And that scared me. Really, really bad.

"Uh, hey, guys ..." I looked around for someone — anyone! — to help me. There wasn't a soul in sight. "I, um, better get back to the ... uh ... thing ...."

But I wasn't going anywhere. Pulling me into the doorway, the delinquent pair seemed to know exactly what they were doing, as though they had planned out this little meeting earlier in the day. Todd was playing watchout, his eyes roaming about, on the lookout for witnesses, while Joe held me up against the wall with a single hand, his face mere inches from mine.

I was doomed

"Stupid fag!" Todd spat. "We saw you showing off on stage today. And now you're running around in a dress? Jesus! You don't know when to quit, do you, fairy boy? You know how stupid you look?"

I knew. I knew exactly how stupid I looked during school. I knew exactly how stupid I looked right then. I wanted to tell him I knew I looked stupid, but I was way too scared to say anything.

"I dunno, dude ... he's lookin' pretty good right now if you ask me," Joe said. "Lookin' better than most of those bitches in the gym. Lookit those cute little tits. And that ass. That's good stuff, man. Looks just like a little pussy. Too bad he's just a little faggot."

I couldn't believe what I was hearing. Unlike Todd's shouting and bullying, Joe's voice was calm and studied, more curious than mean. I was equally shocked to see the serious look on his face; it was as though he had something on his mind. Something he wanted to say to me. For an instant I wondered what that might be.

Then Todd spoke, and my fear returned.

"You might be right, man. He looks okay now, I guess ... for a pussy. Red is my favorite color, you know. Imagine that." I remember seeing a mouthful of teeth flashing just millimeters from my face. "Ain't red your favorite color, Joe?

"It's all right. But ...," the dark teenager moved in so close I could almost taste his breath. "... I wanna see what's really under all this shit ...."

Imagine my horror as my dress was suddenly pulled up high above my waist, up to my chin almost, exposing everything underneath; my girdle, hose, bra ... everything!!! I thought I would die! Nobody but me and my mom were supposed to see me like that!!

How can this be happening?

Being seen in my girlie underwear was the least of my problems. Trapped against the wall, I bit my lip as curious hands started roaming over my body unchecked, poking and pinching and patting me in places only my mother or I had touched.

 

"No-o-o-o ...." I cried. Just like a helpless little girl.

A pair of leering grins only made things worse. "Shit, man, check this out. Maybe this ain't no guy. Maybe he's a real chick. Check out this pussy." Joe rubbed the palm of his hand over my girdle, right where the decorative satin panel hid my pubic area. He was right … I was flat as a girl in front in my girdle, and whenever I'd touched myself in private I'd often wondered if that was what a real girl felt like. Joe apparently found this as fascinating as I did and he felt me up like I was the real thing. I winced when his fingertips pressed against my testicles and made them ache. A second hand joined in, stroking my privates with a practiced rhythm. To my surprise a familiar tingling came to surface and I felt the blood rushing to my cheeks.

Oh, no! I'm getting an erection! I closed my eyes, I was so ashamed.

That's not supposed to feel good! Oh, god ... what's happening to me?

"Cool," Todd said with smirk. "Smooth as silk, and flat ... just like a real pussy. What happened to your balls, fag? Leave them home with mommy?"

"C'mon, guys ... lay off. Umph!" I tried to say something else — I don't remember exactly what — but Joe covered my mouth with his hand.

"Shut up, bitch," he warned. He then licked his forefinger and — before I could stop him — stuck it so far back in my mouth I gagged. He grinned and said, "Here, practice sucking on this for a while! That'll keep you quiet."

While I dealt with this disgusting development unwelcome hands were all over my body again, assaulting me physically and wearing me down mentally. I banged my head against the wall trying to get away from all the pawing and poking that was going on. Getting choked on that stupid finger in my mouth didn't help matters.

At one point Todd slid his hands under my brassiere and massaged my budding breasts ... none too gently, I should say. I panicked and tried to squirm away, but all that did was loosen my clothes and cause him to get a firmer grip on my poor boobs. He seemed impressed by what he felt. "Whoa, dude! He sure feels like a chick to me. A pussy ... these tits ... what more do you need? Let's party!"

"I like that pretty little mouth." Joe pulled the finger from my mouth, licked it lavishly and pressed it back against my lips. The smell of cigarettes made it stink. He then twisted me around and slapped me so hard on either side of my lycra-covered butt it brought tears to my eyes. "Even better, how 'bout a pretty little ass? Now that's prime!"

Hearing those guys talk about me — or, more precisely, my body! — like that was extremely upsetting. But matters got worse when I gasped for air and ended up with that nasty slimy finger back in my mouth. I tried spitting it out, but Joe shoved the tip to the back of my throat and gave me a warning look.

"Don't you dare bite me, bitch, or I'll punch you out. Just suck on it. Do it!" Another hard slap on my tender butt punctuated his demands and started me crying.

In spite of the tears and the hitting and all the tough talk, I couldn't bring myself to do it. Suck, I mean. I knew what that meant, of course. I'd heard the other guys talking about that kind of stuff — oral sex, I mean — and how girls and fags loved doing it. It had never occurred to me to do it and it made me sick to know that someone would think of me that way. I was too scared to spit it out, but I wasn't about to suck on anything, including some guy's finger. My stubbornness, however, didn't stop Joe from shoving his finger around inside my mouth, smearing his spit all over me, ruining my lipstick and making me gag over and over. Between the drool on my chin and the fiery pain on my butt, I felt my stomach churn. I wondered what would happen if I threw up.

Unfortunately, I didn't. Instead, the molestation went on for who knows how long; it could have been thirty seconds, it might have been thirty minutes, but it seemed like ages. I was so ashamed, so confused and I was nearly hysterical. But my tormentors knew how to deal with that; a slap across the face and I stopped struggling. Instead, I concentrated on keeping my wits ... and my dignity.

The boys' focus then changed to getting me out of my underpants. I couldn't believe it as they tried clawing at the tight elastic waistband. And don't think they didn't try! What do they think they're doing? They know I'm a guy, so why are they doing this?

"Goddam, man, what's with this thing? How the fuck did you get it on, fairy boy? Is this somethin' your momma made you wear?" Thank goodness the top of my girdle was so tight neither boy could get their hand down inside. Todd's expression was a mixture of bewilderment and frustration. Joe, on the other hand, seemed more amused than anything else.

"S'all right, dude. We can find some other way to have some fun. We can check out that pussy later."

The panic was indescribable when I realized what they had tried to do, matched only by the humiliation I felt as Todd gave up and returned his hand to the front of my girdle and resumed rubbing the flat satin panel. Joe did likewise to my rear end; my eyes almost popped out of my head as his rude hands cupped my bottom and then something hard — his finger, dummy! — pressed against the lycra covering the crack between my cheeks. Believe me when I say that for the first time in my life I was actually grateful to be wearing a girdle.

Anyway, like I said before, all of this went on for who knows how long. With all the touching going on, I remember bouncing between being aroused and terrified; I couldn't help myself … I was getting an erection under my girdle and my face was red and my breathing was becoming difficult. I hated Todd and Joe for making me feel that way. I also remember someone — Joe, I later figured out — taking my hand and pulling it downward. Imagine my surprise when the palm of my hand was rubbed over the front of somebody's pants. At first I didn't know what I was feeling, it was so long and hard and …!

Omigosh!

My mouth went dry when I realized I'd just touched a penis. Granted, it was underneath a pair of jeans and all, but that didn't make it any less significant. It was some guy's dick! Gag! I couldn't believe what was happening. I mean, talk about being confused … It was a lot larger and warmer than mine had ever been … a sensation I'd never forget ... no matter how hard I'd try.

"See there, bitch?" Joe said with a grin. "You can't be no fairy, 'cause you got me all hard. And I ain't no fairy. So you know what that means, dontcha?" I know I must have looked like a fool, shaking my head with his finger still in my mouth. I didn't have any idea what I was expected to say. "It means you're a bitch, that's what. And since you're a bitch, you're going to have to do something 'bout this!"

I didn't know what "this" meant. At least until my hand was placed on the front of Joe's pants once more. Feeling the heat coming from underneath, I suddenly understood.

"Open it up," the black youth ordered quietly. "Do it, girlfriend, unless you like being slapped around some more."

I shut my eyes. I couldn't believe it. He wants me to jack him off! Maybe if I keep my eyes closed long enough, I thought, and maybe if I prayed hard enough these two freaks would get tired, or bored, and leave me alone. I don't want to jack this guy off! If I do that … who knows what'll happen after that! Please, god … help!

MOM!!!!

SLAP!!! A fierce whack on my aching butt woke me up. Todd was saying something about how I might rather practice sucking some more, and Joe's face lit up with a big grin. My fingers traced the outline of his erection, edging toward his zipper when I heard a familiar voice echoing down the hall ….

"Greg ...? Sweetheart, is that you down there? What's going on?"

 

Chapter 25 — A Grateful "Girlfriend"

 

There was a long silence, the only sound in the hall my own labored breathing. I waited, half hoping, half terrified, desperate for something to happen and worried about the consequences if it did.

"Greg?" The voice sounded softer, further away. "Pamela …?"

At last there was the sound of sneakers squeaking on tile, and I was found.

"GREG???"

Kathy's eyes went wide and her mouth dropped open. No wonder. I mean, there I was, standing against the wall, my makeup all smeared, with my dress up around my waist and my girdle prominently on display. I was surprised she didn't burst out laughing right then and there.

Where were the boys, you ask? Gone, of course. The instant Kathy appeared they'd turned tail, disappearing down the hall and leaving me alone and looking like an idiot.

My date looked me up and down and frowned. "What's going on? Who was that? Are you all right?"

I fumbled with my dress, trying to get it down before she got too close. I failed miserably. In fact, Kathy ended up untangling the hem from where it had gotten stuck in the waistband of my girdle. I was too upset to figure it out myself.

"Now how'd that happen?" she asked, her brow furrowed. "Why did you have your dress up like that? You weren't showing off for those jerks were you?"

"Huh? Showing off?" I couldn't believe what I was hearing! "Kathy! I wasn't showing off! Didn't you see what was going on? Those stupid idiots ... they almost ... almost ...." I couldn't think of a word to describe what it was they were doing to me.

That didn't stop me from crying, though. I was both mad and scared, and I ranted and raved for a few minutes, looking like a fool in the process, I'm sure. Occasionally throughout my tirade Kathy would give me a skeptical look, which made everything worse. I'd really wanted her to like me and here those jerks had to go and ruin everything! Why didn't she understand what had happened just then? Couldn't things go my way just once?

"I hated it!" I cried. "I hate them! They touched me … all over …. I was so scared … it was the worst thing that ever happened …." I was sobbing so hard I got choked and couldn't say anything else.

By the time I was done fussing and crying Kathy was a little more sympathetic. She helped me straighten up and fix my make-up and get my dress back together. Ashamed as I was, I couldn't help feeling more than a little flattered to find myself the focus of so much attention from such a pretty girl. Thinking about it later, I decided that she must have enjoyed seeing me so upset. I mean, she seemed to really care about me, but there was a definite mean streak there.

"Poor thing ... you were really terrified, weren't you? Well, don't worry … I won't let anything else happen to you."

That seemed like a funny thing to hear a girl say, but it actually made me feel kinda good. "I'm better now, I guess. The night started out kinda fun at first, but not any more." I sighed. "Girls sure have to put up with a lot of crap."

"Oh, it's not always so bad. You like it when you're with me, don't you?" Kathy held my hands in hers and gave me a long look in the eye. As upset as I'd been just a few moments before, I felt like melting right then and there.

It took a while to get me put back together, but we eventually got back and joined in the dancing as though nothing had happened. A couple of her friends asked where we'd been for so long, and when she said "None of your business," they made kissy faces at us. She thought that was pretty funny, but for some reason I felt embarrassed.

I was almost sorry when the lights went back up at eleven and we made our way to find our shoes. Kathy was able to sit down on the floor to put hers on while my short skirt prevented me from assuming such a risqué position. I had to hold onto the side of the rolled-up benches to slip them on, and then keep my back to the wall as I bent forward to fasten the buckles. After all I'd been through, I wasn't about to show my lace-covered butt to anybody else!

We made our way back to the rendezvous point, but Mom had not yet arrived. Kathy turned to me and said that a good night kiss would be awkward on the front porch in view of my mother. Her frankness caught me off guard and I was stunned when she put her arms around my waist and placed her mouth against mine.

"Ummm, your lips are so nice and soft, ‘Pamela’," she seductively cooed. "I've always wanted to kiss a pretty girl like you …."

As we kissed I felt her tongue parting my lips and entering my mouth. At long last, my dream was coming true! I instinctively started to gently draw that wonderfully warm, wet thing into my mouth and experienced my first French kiss. I have to admit … it wasn't at all like my little practice sessions in front of the dressing mirror. It felt like someone — or some thing — was attempting to invade my body through my mouth! How fantastic that feeling was to me!

It didn’t end there. My entire soul melted under Kathy's curious probing. She then slid her leg between mine, forcing herself further inward. Pressed up against a guardrail, I made a little cooing sound as I tried to press my knees together. I couldn't help thinking of how I'd been by Todd and Joe, and the shame I felt earlier returned. That didn't stop my date, though; she turned even more aggressive, spreading my legs apart until she was rubbing the front of my panty girdle through my dress. Burdened with my purse and bangles, I held my hands up in the air, open to her advances.

This went on for so long that I developed trouble breathing. Between the kissing and the feeling of her body against mine, I was powerless. This wasn't at all like how Todd and Joe made me feel! My passion soon built to where I felt a shudder between my legs, and I couldn’t help squeezing my legs around Kathy’s in reflex. I opened my eyes in time to see hers open. She gave a little laugh as her hand slid up my leg and pressed against the flat panel on the front of my panty girdle.

"I just love your girdle!" she said, delighted at her discovery. She rubbed the satin panel covering my front and giggled. To be fondled so intimately was shocking, I was so mortified, I thought I was going to die! "I knew it felt like something was missing down there! Ummm … you’re so warm right there, just like a girl should be. This is great!"

Funny thing, that. I mean, here Kathy was, saying almost exactly the same stuff about me that those two jerks said a little while before, but coming from her it was like a compliment. Boy, I was really confused, but I didn't have much time to worry about it.

Kathy pressed her lips against mine one more time and I found myself squirming helplessly from top to bottom as her hands slid freely under my dress. I couldn't help but wince when she pinched the tender skin between the tops of my stocking and my girdle.

"You don't know how many times boys have done that to me," she said with a giggle. "Now it's my turn to have some fun."

I made a little "Ow!" sound as she pinched the vulnerable flesh again, but I didn’t do anything else; I know this sounds weird, but as much as it hurt, I almost wanted her to touch me like that all night long.

It ended as headlights swung around the turnout and my mom’s car pulled up next to us. I don’t know if she had seen us, but I would probably find out later if she had. Knees weak and hands trembling, I struggled to pull my dress into some semblance of order. When my eyes focused on Kathy, I could see the remnants of my lipstick on her mouth. Mom would probably think it was hers … I hoped.

It was principally Kathy and Mom talking on the ride back to her place. I was too shaken to trust myself to say anything. Kathy couldn’t have been more complementary about how I danced and acted my part that evening. She even went a little bit overboard when she told my mother that I was too pretty to have been born a boy. Talk about betraying inside information! My mother just glowed with happiness to hear such things being said about me.

When we arrived at her home, I walked her to the door, gave her a quick kiss goodnight and watched as she disappeared through the door. I got back in the car exhausted from the length of the day, and we drove home with hardly a word spoken.

As I undressed, Mom was there to help me take off and hang up my new clothes. The underwear went into the dirty clothes straightaway; I was terrified my mother would see the sticky wet stain in my panties from where Kathy had gotten me all excited. I made a mental note to do the laundry first thing in the morning, just to make sure she didn't see what I'd done. I then creamed off my makeup for the second time in one day. With my hair finally down and in my own pajamas, I started feeling human again.

As usual, Mom quizzed me pretty thoroughly about my date. She asked me if I danced any and if Kathy and I kissed, you name it. I tried avoiding telling her everything, but the look in her eyes stopped me from lying. I confessed to the dancing and kissing, and when I admitted having a good time as "Pamela," she responded a nod and an evil smile.

"I knew you would, even if you didn't want to admit it."

As we chatted Mom eventually asked me about Todd and Joe. That put a chill down my spine, and when I tried brushing off her question, she insisted that I tell her what happened. I couldn't believe it! It was as though she'd been spying on me the entire evening!!! When I confessed that they'd picked on me some, she got a funny look on her face. It appeared as though she was about to burst out laughing. The more she questioned me the more I confessed to her, and the more knowledgeable her questions became. Eventually I spilled my guts and told her the entire story about getting caught in the hallway and molested. I had to describe everything, how my dress got pulled up, how Todd slid his hands up my bra, and how both boys rubbed me between the legs. I didn't dare admit that I'd gotten a little bit aroused when the guys touched me like that; nor did I mention how Joe had made me suck his finger. If my mom had known any of that stuff she would have never let me live it down. I'd have rather died than go through all of that! Instead, I just broke down and cried when she asked me what it was like to be touched by another boy. The tears were real enough, that's for sure. And that seemed to make her happy enough.

 

After my interrogation we shared a few cookies and some warm milk and then I went to bed. I was asleep before my head hit the pillow, and my dreams were as confusing and rousing as those I can ever recall.

The rest of the weekend was anticlimactic. I couldn’t get my mind off Kathy and I called and talked with her Saturday evening. She wanted to know what I was wearing and I lied and told her jeans and my baseball jersey. She said she didn’t believe me and threatened to ask my mom, who was listening in on the extension, thank you very much. I confessed that, well yes, I was still wearing a dress and a bra, too, but not the padded one I had on Friday.

"Well, sometimes Mom has me wear a training bra for reasons only she knows," I fibbed. "Pretty stupid, huh?"

"Oh, maybe a little bit," Kathy said with a giggle. "But that's all right. I like cute boys … in cute clothes …."

Kathy kept pressing me and I finally also admitted that I was still sporting my long nails, but I told her that Mom had let me change the color to a light pink. My date reassured me that she wouldn’t tattle at school and said something about liking my gentle ways.

"I hope we can stay close friends," she said.

"Me too. I really like you, Kathy," I told her.

When Sunday night came, my nail extensions were trimmed back to a near normal length, my earrings returned to my desk drawer, and my hair washed and almost restored to its former simple style (except for the bangs). By next morning I was back to being Greg.

When I got on the bus there was an empty seat waiting for me next to Kathy and a warm smile on her face. She looked really great and on that day it was she who was wearing a dress and makeup. Things were looking up. I sat down next to her and took in the clean pleasant scent radiating from her. I closed my eyes and could have been in heaven.

Maybe the nightmare was at an end ….

 

Continue with Chapter 26 of "Lipstick Discipline"

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