This transgender story contains adult themes dealing with female to male crossdressing. Its got naughty language and naughty bits, too. If you are too young to read such a story, if you are offended by such themes, or if its illegal to read this where you are, then don't read any further.
On the other hand, if you like it, if girls in guy's clothes turn you on, then let me know! Cause thats what I like too!
This original story is copyright (c) 1999 by Kozmik Alaska
The Incredible True Adventures of the Two Girls Who Went to the Prom Together
by Kozmic Alaska
----------------------------------- CHAPTER 1 -- Ow! -----------------------------------
Spring was in the air, and for the seniors at Enright High School, this meant three things, finals, graduation, and the senior prom. For Carole Jackson this meant attending that prom with her boyfriend, the coolest guy in pants, or out of them preferably, Bill O'Brien. Bill was cool because he was drop dead handsome, and a freshman at McKnight Academy at the other end of the state. To a status conscious 18-year-old, dating an older guy may have been enough of a status symbol, but to be dating a McKnight man was the ultimate.
Carole also considered that she had a particular edge with Bill, because she was best friends with his twin sister, Jill. As kids, the twin's mom used to dress them alike, almost as a taunting challenge to the world to tell them apart. This left the twins with the difficult work of developing their own separate identities. As things go, Jill and Bill always seemed to have an insight in each other's inner thoughts. Carole relied on this to find out what was ticking in Bill's head. She'd just confide in Jill. Jill's sixth sense about Bill came in quite handy.
It was no surprise on Thursday evening when Carole and Jill were at Valley Mall, that when Jill felt a blow to her head and the resulting sharp pain it meant big trouble for Bill.
'Ow! Cripes! What the hell was that!", Jill screamed. She felt a bit of dizziness, and sat on a bench.
'Are you okay?' Carole asked.
Jill hesitatingly said, 'I.. think .. so. I just feel like my bell got rung. Perhaps we had better head home. I think you should drive.' Jill tossed her car keys to Carole.
When they returned to Jill's house, they discovered just what that sharp blow was all about. Jill's mom and dad had left a note indicating that they had rushed off to the hospital at McKnight Academy over on the other side of the state. Bill had cracked his head after going over the handlebars on his bike when he drove it into a sewer grate along the road near his dorm. The note went onto say that their parents had driven off across the state to get Bill and would be bringing him back from school on Sunday.
'Arrrggghh', Carole sobbed. 'Poor Bill. Poor Me. No prom! Whaaaa!'
Jill tried to comfort her buddy. 'Ah. I'm so sorry Carole. This is a disaster. Here's a Kleenex. We'll figure something out.'
Carole sat on Jill's bed crying and wiping her nose.
'Now I'll never get to go to the senior prom. And my dear poor Bill, he must be in so much pain, the poor dear.'
'Maybe we can arrange a prom date for you, Carole" Jill offered.
'Wah! I don't another date, I want my Bill! I wish I could just clone him.' Carole cried.
The two girls sat there, as Jill hugged Carole, 'There, there, Carole...hey wait, I have an idea. Maybe we can clone Bill."
Jill went over to her desk drawer and dug around. 'Ah there it is. Take a look at this, Carole'
Jill handed Carole a picture of two girls. The girl of the left was Jill in her Girl Scout uniform from back in junior high. But the one on the right was also Jill in her Girl Scout uniform. 'Meet Jill and Bill O'Brien -- Members of Girl Scout Troop 114!'
Carole giggled at the thought of Bill being a Girl Scout. "When was this?" she asked
'Back in 7th grade, for Bill's BOY Scout troop's Halloween party. My mom thought it would be a trip if we BOTH went as girl scouts. That way we'd keep people guessing just who was the real Bill!"
'Bill's really cute, isn't he?' Carole snickered.
'Yep! I helped him get ready for it. Mom even bought us matching training bras and panties. She made Bill wear a training bra and panties for a week before the party just to get used to it. He wasn't too pleased. I knew he was a bit miffed, so helped him as much as I could.'
'By not making fun of him?'
'ESPECIALLY by not making fun of him. So now it look like its a karmic turn of sorts.'
'Whaddya mean?', Carole said still giggling.
Lowering her voice, Jill said, "Hi I'm Bill O'Brien. Want to go to the prom with me..."
'Ah, Jillie, maybe that pain in your head did a bit of damage. Perhaps you better have a lie down.' Carole said.
'No, Carole, I'm serious. It'll be fun. I haven't been back to Enright High since I started college. I'm all done with exams, so let's do it.'
'But Jill, what about a tux, and ... those?' Carole pointed to Jill's small A-cup breasts.
Jill looked down at her chest. 'A tight undershirt ought to take care of them. Plus Bill and are about the same size and mom picked up his tux the other day. It's hanging in his closet. So, will you allow me to escort you to the prom, Miss Jackson?'
Carole tilted her head, scrunched up her nose, and smiled. 'Well.... Alright then.'
Jill let out a little laugh, clicked her tongue, and rubbed her hands together. 'Okey dokey, its a date then, I'll pick you up at 6. I have some work to do, so please allow me to begin my transformation.'
Carole got up from the bed, and looked back at Jill. "Are you sure you want to do this?'
'You betcha, sweetheart.' said Jill as she assumed a masculine stance.
'I'll see you tomorrow, handsome.' Carole said as she blew a kiss to Jill.
----------------------------------- CHAPTER 2 -- Jill to Bill -----------------------------------
After Carole had left, Jill set about getting mentally prepared for her role. She entered Bill's old bedroom, and took the sharp looking black tux out of closet. She ran her fingers along the lapel and imagined herself wearing it. She picked up the shiny black dress shoes and then pulled one on. Not too different from the funky shoes she'd been wearing at school, Jill thought.
She made her way over to his chest of drawers. The top drawer was filled with socks. She pulled out a black pair and set them aside. The next drawer held Bill's underwear. Jill pulled out a pair of white Fruit of the Loom briefs. She held them in front of her. This funny little hole in the front sure is interesting, she thought.
Jill made a mental note, ''I'll wear these tomorrow.'
Setting them aside, she dug further and pulled out a strange looking thing. It had a pouch in the front and two straps that extended around to back and attached to the wide elastic waistband. The label above the pouch said 'Bike -- the original jockstrap'
'Ah, so that's what a jockstrap is,' thought Jill. 'I wonder...'
She quickly pulled off her shorts and top. Jill pulled the jock up her legs and adjusted its pouch over her pussy. Reached behind her she pulled the taut straps down over the cheeks of her rear.
'There we go...I'm a jock!' she chuckled. 'Well almost one, something IS still missing.'
Jill strutted about her brother's bedroom. She swaggered over to her to her brother's bed. After turning in down, she climbed in, still wearing just the jock, and pulled the sheet around her. She reached over to the nightstand and turned out the light.
As Jill lay in her brother's bed she began to drift off. Soon the darkness enveloped her, and she fell to a deep dream filled sleep. In her dream, Jill imagined her hand drifting down to her crotch. She felt the rough material of the pouch of the jockstrap. She thrust her hand into her jockstrap and began massaging her clitoris. She felt it harden at the touch of her fingers. She then slid her middle finger down between her vaginal lips. As she began to rub faster, she felt her clit grow more erect. Somehow it felt different tonight. The skin of her labia began to feel a bit flabby and wrinkly as her clitoris grew to the point that it extended outside the pouch of her jockstrap. Unconsciously her rubbing turned to up and down strokes as began pumping the dick her clitoris had turned into. Her rhythm steadied as her balls tightened. Jill's head grew light as a pleasant feeling like a mild electric shock went down from the top of her head and up from her toes, meeting in the head of her erect penis.
The sperm flew high as Jill suddenly leapt up from the pillow and yelled out, 'Yi yi yi!' What the hell was that.'
Now wide-awake, Jill realized what was missing.
----------------------------------- CHAPTER 3 -- Prom Night -----------------------------------
Jill spent Friday running around getting ready. At 10AM she spoke with Carole on the phone.
'Are you all ready, my dreamboat?' Jill asked.
'Well, I have to get my nails done, and then finish my hair.' Carole replied. 'How about you?'
'Well, I had a brainstorm of sorts last night. I have just one last thing to buy, then I'll be set.' Jill answered.
'Then I'll see you at 6.' said Carole.
'See ya, gotta run', said Jill.
At 4 PM Jill stood in front of the bathroom mirror, a towel wrapped around her waist. She tossed towel to the floor and reached over to pick up the pair of white boy's briefs she had set aside for herself the night before. Admiring herself in the mirror she explored that funny little fly opening the front. She slide her hand into it and felt her bush. Enough of that, Jill thought.
Jill picked up a can of shaving cream in her left hand. After shaking it she squirted its contents into her hand and then spread the soapy white lather onto her cheeks and chin. Picking up the razor she bought earlier in the day, she began to shave her face. First her cheeks, then her neck and under her chin. Ever so carefully she shaved under her nose. 'I mustn't cut myself', she thought.
After washing off her face, Jill splashed on a bit of aftershave. Again she stopped and admired herself in mirror, standing there wearing only her white boy's briefs. 'Whoa!', she remarked out loud, 'Almost forgot my pal.'
Jill headed off to her brother's bedroom.
At 6 PM sharp, Jill nervously rang the doorbell to Carole's house. If she could pass the test of the dreaded parents, she could pull this off. Carole's dad answered the door.
'Come right in young man.' he said motioning to the living room.
'Honey, Bill's here for Carole.' He shouted.
'Whew!' thought Jill, 'I think I did it'
As Jill and Carole's dad engaged in some small talk about school, Carole made grand her grand entrance. She looked lovely.
'J..Bill! You look great.' Carole exclaimed. She examined Jill from head to toe. If she hadn't known what was going on, she'd have sworn it really was Bill.
After pictures and pleasantries, Carole and Jill headed off to prom. A grand time was had by all. As they danced a slow dance Jill pulled Carole close to her. Carole could smell the lingering scent of Jill's aftershave. As they slowly swayed to the music, Carole also swore that she could feel something hard rubbing against the front of her dress. Carole felt a familiar wetness in her panties, and was sure she was just imagining that she really was with Bill. Jill began to rub and grind against Carole just as the music ended. They both looked at each other for a second.
Snapping to her senses, Carole said, 'I think I have to go to the girl's room, how about you. The rum you spiked our cokes with is starting to hit'
Jill smiled, 'Uh, I don't think so. I think I better use the boy's restroom.'
'Yeah, ' Jill chuckled, 'you're right.'
Carole sat in one of the stalls in the girl's restroom. Around her she could hear the other girls.
'Did you see that Bill O'Brien. He's a hunk.'
Carole stifled a laugh as she thought, 'If only they knew.'
'I bet he's hung like a horse.'
Again Carole chuckled as she thought, 'If only they REALLY knew.'
Carole pulled up her panties, flushed and opened the stall door just as one of the girls said something about giving anything to feel Bill deep inside her.
'Hi girls,' Carole said in a catty voice, 'Enjoying the prom?'
Meanwhile, in the boy's room Jill strode over to a urinal. Out of the corner of her eye she observed the other guys. 'Wow, Jeremy Hamilton sure is tiny!' she thought. She fumbled with the zipper of her pants and pulled in close to the urinal. 'Okay', she thought, 'I'll fake it.' She made a few hand motions and then zipped up. Spinning around as she flushed the urinal, she found herself face to face with another boy.
'Hey Billy boy, how's the fellow. Gonna get some from Carole Jackson tonight?'
Jill grabbed her crotch and clicked her tongue, 'You betcha!'
After the prom Carole and Jill drove to Hunter's Point. Jill tuned the radio to a soft station as Carole laid her head Jill's shoulder.
'I can't believe we pulled it off' Carole said.
'The night is still young', said Jill.
Jill reached over a guided Carole's hand to her crotch. Still a bit light headed from the rum she had earlier, Carole cupped the bulge in Jill's pants. Jill leaned over and kissed Carole, thrusting her tongue into Carole's mouth. Carole squeezed on Jill's manhood.
'Yeah baby, take it out,' Jill whispered into Carole's ear.
Carole undid the snaps on Jill's pants and pulled down the zipper. She reached in and ran her hand along the stitching of the fly of Jill's boy's briefs. Slowly she slid her hand past the waistband, and felt Jill's surprise.
Snapping to attention, Carole said, 'Jill, its a ...you've got a....'
'Hush...or everyone will want one! It called a slide on tool. I bought it at the adult bookstore down town. Pretty real, huh?' said Jill.
Jill pulled the head of her fake dick out through the fly hole of her boy's briefs.
'Wow, I'll say,' marveled Carole.
'And I think I know how to use it, too,' said Jill, 'that is, if you want to.'
Carole nodded an okay as she reclined her seat. She pulled her panties down to her ankles as Jill whipped off her pants and boy's briefs. Carole marveled at the equipment that Jill sported. It even had testicles and hair!
Soon Jill was on top of Carole. Gently she glided her penis into Carole's slick vagina. As they began thrusting in and out, Carole answering Jill's every stroke; Carole could feel Jill's balls bouncing off her pussy. The air filled with their moans and pants. Jill felt her mind drift and began to actually feel the build up in her balls, now tight and heavy. Together they moaned and exploded as Jill made that one last deep thrust.
----------------------------------- EPILOGUE -----------------------------------
Jill and Carole waited for Bill to return from school on Sunday. When he walked through the door, Carole ran up to him, hugged him and then kissed him deeply.
'Oh honey, I'm so sorry about the prom,' he said.
Carole answered, 'I know, baby, I know. Are you all right, sweetie?'
'Yeah, I'm okay, but boy did I have the weirdest dreams on Thursday and Friday nights.', Bill said.
Carole looked over at Jill. Jill stood there, smiling, all-knowing.