This is an original story of mine for viewing by mature adults who are not offended by sexual content or by transgendered themes. Hope you enjoy.
The Prom Queen (TV,Mm)
There it was, the long floor length bronze coloured satin dress with the hip high slit on the left front. Beautifully trimmed in satin copper and black velvet. I could hardly believe they had another. It was a size 5 too, perfect. The sales lady came over to me, "Can I help you?" she asked.
I wondered if she remembered me from four months ago. I want to buy this dress, and some black gloves too. She seemed to remember now, "Oh yes, I remember now, your girlfriend looked lovely in this dress, are you getting her another? If she needs adjusting, we can do that for her instead of buying a new one," the sales lady continued.
"Sorry, its not for her this time," I replied with a smile. I don't know if she thought I was a heel or if she actually had figured out the truth, that the dress was actually for me.
Yes it was only four short months ago, senior prom. I had been a best friend with my next-door neighbour Kelly for a year. We did everything together, almost everything. Kelly treated me like a girl friend, telling me all her secrets and hanging out with me. I always critiqued her clothes, as she valued my opinion. It felt good to be friends with the best looking girl in school but I still wanted more. Being small and frail for a boy my age was difficult. I got picked on a lot by the jocks and bullies but spending so much time with Kelly made gave me credentials and didn't face so much abuse. I wanted to ask her out to the prom so bad, but I was scared as hell that she would say no. We had never even kissed, so I had no idea if she even interested in me like that. Her other friend, Rhonda, captain of the girls soccer team, who was kind of stocky and had short hair was interested in me. She made a point of letting me know. I sometimes found it difficult to avoid her. My only interest was Kelly, pretty, model figure, high cheek boned, perfect skin, long red hair, Kelly. I lost track of how many nights I went to bed beating off to Kelly's perfect image.
It was getting close to prom and all we could talk about was what she would wear. I envisioned her in metallic colours, bronze maybe. We went shopping on a Saturday as we often did, and found the dress, I showed her and she loved it. She tried it on and I thought I was in love. She looked near perfect. Just some black stockings, the right shoes and accessories and she would be. It was at that moment that I summoned up all my courage and asked her if she would be my date at the prom. Kelly looked at me and giggled. "Marty, don't be silly, you know Brad already asked me. You did didn't you?" she suddenly turned compassionate realizing she was tearing out my heart.
"Oh yeah, I knew, I was just, you know in awe of you just now," I retreated, not wanting to loose my friend over an impossible dream.
"I figured you and Rhonda were going together anyway, I mean the four of us will sit together of course," she went on. My heart had been torn out but I forced a smile out of friendship and agreed with her. "Just save me a dance then will you?" I asked. She agreed and that was that. I did go with big Rhonda and Kelly went with Brad, the handsome jock. They were voted King and Queen of course while I was stuck with Attila in her horrid pastel pink bridesmaid wanna be dress. It was a predictable evening, dancing, drinking, the motel room, Rhonda `making me a man' much to my dismay.
The next day it finally dawned on me as I watched Brad kiss Kelly goodbye, that I wasn't jealous of Brad, not at all. I was instead jealous of Kelly. I imagined that it was me as prom queen, the centre of attention, looking as pretty as Kelly. I imagined that I would have done a better job anyway. She always needed me for fashion advice, fixing her hair and I was always helping her with her makeup. Without me she was just another plane Jane.
I remembered that my house was Sunday morning and the rest of the family had gone to church so I ran upstairs and started putting on some of my mother's clothes. I was right; I would make a prettier girl than Kelly. From that point on, I secretly dressed up whenever I could. I practiced wearing makeup, walking in high heels, and painting my nails. I did this all summer and began building up a small wardrobe, which included sexy black lingerie, which was my favourite of course. I even went downtown and purchased C-cup breast forms and a gorgeous long redhead wig. It was hard hiding it all from my family but I had to. My dad would have killed me if he found out. I wasn't worried too much as I was off to college in September and would be living alone for the first time and would be free to dress up as I pleased.
Finally I was in college and thought I might be free at last but there was a hitch. My dad insisted that in order to receive my tuition money from him I would have to pledge his old fraternity. He figured that would make me a real man I guess, as I am sure he had his doubts. I didn't want to but would have do as I was told to get my money. I rationalized that I didn't have to make it but I only had to pledge. I would put in a halfhearted effort and they would reject me and I would again be free to live in my own apartment where I could dress up whenever I pleased, which would be often.
Pledging was horrible and I hated it. It was humiliating and terrifying but I figured it would soon be over. My `big brother' was Andy who was actually all right. He was nicer than the others. Andy was Engineering major, senior, who had no trouble with girls, as he was very fit, blond, blue eyes and swam on the school team. Sometimes when things got rough, Andy would help me out. One day they told all of us pledges that there would be a formal dance that weekend and we would be required to dress as women for the night. It was all part of the humiliation process, making us dress in drag for a crowded room of people. It would be a good laugh for everyone but it affected me differently. I suddenly found myself not wanting to dress up for once. Andy seemed eager about it all, asking if I needed help finding something to wear. I told him no, and decided to just go for it.
So I found my way back home and to the same dress shop that Kelly and I got her prom dress from. I was amazed that they had another one just like it. I bought it, black velvet gloves, black ankle strap, patent leather CFMPs, bracelets and a great faux pearl three-strand choker with matching earrings. I went to the drug store and bought matching bronze lipstick and copper roof eye shadow. I was determined and focused like I had never been before to be the girl of my own dreams.
I spent all day getting ready for the big evening, shaving my legs and arm pits, plucking my eyebrows, doing my toenails and finger nails, a deep mauve colour that was perfect. I had brushed my wig to a shine then fastened it snug to my own hair so it wouldn't fall off easily. I parted it to the side with the bangs hanging a bit over one eye. I wore a hair band on top. I then put on my makeup to perfection, followed by the garter belt, seemed stockings, lace panties, stuffed bra, and finally, the dress and accessories. I gave myself a squirt of Obsession perfume and gazed into the mirror. I could not believe my eyes. I was twice as gorgeous as Kelly looked on prom night. I fetched my black velvet clutch and grabbed a taxi.
I arrived at the frat house with nervous trepidation. I took a deep breath and concentrated on looking elegant. I glided into the room quietly and heads began to turn. One after another, the half drunk frat boys stopped in shock and their jaws dropped to the floor. No one had said anything to me by the time I made it to the bar and the noise in the room had been cut in half as if by a sharp knife. No one had recognized me yet, even though they were all staring at me. The other pledges were lined up at the bar as well, all dressed in drag. They looked kind of scary too. Most had bad house dresses that they got from their mothers that fit poorly, and had hairy legs, bad Dolly Parton wigs, Bozo the Clown makeup and tennis shoes. It was a pitiful display but it centred me out as the different one.
Finally Andy arrived and smiling inquisitively asked, "Marty? Is that you?"
I winked a reply. Andy was dressed smartly in sensible clothes and his hair was groomed perfectly. Standing next to him in my high heels I was still not as tall as his 6'0" frame. He handed me a drink and he made a big fuss over me telling me what a good job I had done dressing up. It was obvious that I was no novice at this and I didn't care if anyone thought so.
The evening included a lot of silly games like `drag races' and such which I put very little effort into. I didn't win anything and was only concerned with not messing my makeup or staining my dress. After the games, there was music and dancing. A few sorority girls were there, girlfriends of the brothers, but it was mostly guys. Andy was quick to get me on the dance floor and continued to compliment me on my incredible appearance. I had fixed my makeup several times in order to look my best. During the night several other frat boys lined up to dance with me all of whom would tell me how good looking I was. During a slow dance late in the night, Andy had pulled me close to him and let his body press into mine. He nuzzled up against my cheek and I could feel his warm breath on my neck and his hard bulge against my abdomen. His hands roamed over my back and my ass. I could not explain the feeling I was getting, but my body was getting warm and I was feeling a bit dizzy. When the song was over, they announced one more prize. It was the beauty contest and I was the winner. They gave me a crown and a bouquet of roses. I paraded around one more time to all there applause. I admit that I loved the feeling and the attention; even it was just a stupid frat game.
I searched for Andy and asked if I could leave. I was feeling overwhelmed and wanted to go home and take it all in. Andy volunteered to take me back to my apartment. He was a total gentleman. Out front of the building Andy stopped the car. He told me that the other brothers didn't want me in, but that he could sway the vote and get me in. I admitted to him that I didn't really want in anyway and for him to not go out on a limb for me. He indicated again how attractive I looked to him and how much he enjoyed dancing with me, which made me blush. He leaned closer to me and I naturally leaned toward him. His soft but strong lips pressed against mine and the feeling of electricity ran thru my body. He was kissing me full on and I loved it. His lips were gentle yet in control. His tongue probed my open mouth and I melted into his arms. I didn't have a lot of experience kissing girls but none compared to my first kiss with a guy, which was out of this world. I completely lost track of all time and other senses while I made out with Andy.
Our kissing became more passionate and intense. He held my head and ran his fingers thru my long red tresses as he half climbed on top of me. I never let go of his mouth as we awkwardly adjusted ourselves in the car. I yearned for his tongue inside my mouth. He was so passionate and so sweet. At one point I felt his hardness pressing against my leg. Some how my hand accidentally slipped and landed on it. It felt so big and long. I stroked it thru his pants as if unconscious of my actions. His cock was throbbing and I found myself wanting more. As if on queue, Andy moved a little and unfastened his trousers and pulled down his zipper. I kept sucking on his bottom lip while he freed his big cock. It was so thick and lovely. I stared at it for a minute in awe of its presence. My own cock, buried in my tight panties was equally hard but I kept it tucked away trying to remain as lady like as I could.
I had hardly noticed that we had stopped kissing as I subconsciously drew closer and closer to Andy's swollen member. My mouth was open and filled with saliva and like a magnet it closed the distance to Andy's cock. My dark lips encircled his purple head. My tongue darted out to taste the little dollop of precum on it. It tasted sweeter than honey to me, and I engulfed as much of the penis as my mouth would allow. I had to have that cock in my mouth. I started sucking and getting it nice and wet; my gloved hand pumped the base of the shaft as my tongue ran up and down the length of the shaft. It felt so good. My throat began to relax as his fat cockhead penetrated deeper inside. I could not believe that I was sucking cock. I had never even fantasized about it. But it was meant to be. I wanted to give Andy the best head he ever had so I sucked and pumped with everything I had. Andy responded by fucking with his hips. He was growing shorter of breath and gritting his teeth. I knew he was close so I just sucked him harder. Soon he held on tight to my head and injected my mouth with burst after burst of hot, salty cum. I swallowed and swallowed until his balls were spent and my hunger was satiated with his love sauce.
After regaining our composure and our clothes, Andy gave me a sweet gentle kiss. He then walked me to my apartment like a true gentleman. We began making out again at the door and was really feeling up my sexy ass. I could feel that he was starting to get stiff again. "Oh Mary, I want you sweetheart, I want to get inside you," Andy whispered into my ear.
"You want to fuck me?" I asked in a surprised voice as was not ready for this step just yet. He devilishly grinned and nodded yes. Not quite sure that I could handle yet I slowly separated us. "Well, as good as that sounds lover, I'm not quite that easy, you'll have to take me out on another date first," I finally replied while giving him one last kiss. Andy agreed and set a date with `Mary' for eight the next night. I have to admit that it was difficult making him wait one whole day but I really wanted to see him again. I spent the night dreaming of him fucking me while I masturbated half a dozen times.
It would be worth it, because Andy was eager to date me and I could sense that something bigger was in store for us both. For one night I truly was the prom queen. I will save the rest for the next story. Hey, I'm not that easy!
Marty