Kylie and Chrissy by kdarling
Summary:

Two teenagers discover their feminine alter-egos and embark on a crossdressing journey together. 


Categories: Fiction Characters: None
Age Group: Adult to College Age AR
Categories: Crossdressing/TV
Genre: Erotica
Keywords: School Girl
Story Universe: None
Challenges: None
Series: None
Chapters: 1 Completed: No Word count: 2558 Read: 902 Published: 02 Jan 2017 Updated: 23 May 2018

1. Chapter 1 by kdarling

Chapter 1 by kdarling

�Stop� we really shouldn�t be doing this�

�It�s just a bit of fun. Now just hold still while I do yours�

�Ok, but only for a few minutes, what if we get caught?�

�They won�t be home for hours, just relax�

�How long have you actually been doing this?�

�A while� do you like it?�

�I don�t know. Doesn�t your sister know?

�Nah, why would she?�

Applying a final layer of lip-gloss to his friend�s lips, Chris leant back and passed a vanity mirror to Kyle, �what do you think?� he asked. Both boys sat crossed legged on the carpeted floor of a dimly lit bedroom, their stocking covered knees overlapping.�

�I don�t know, I feel weird� Kyle responded.

�You shouldn�t. You look good�

�It�s not that. It�s this. Isn�t it a bit, you know� gay?�

�How can looking like a girl be gay?� Chris moved closer to Kyle, gently taking hold of the other boy�s hands and placing them in his own. �Just relax, we can stop at any time�, he whispered before moving into to kiss Kyle softly on the lips. As lip-gloss covered lips met lip-gloss covered lips, Kyle felt a surge of overwhelming electricity shudder through his body, and his already hard penis strained against the pink satin lingerie.�

�Don�t fight it� Chris whispered before the two passionately embraced each other.

-

The next day, Kyle Anderson woke up late.�

The summer holidays were beginning to come to an inevitable climax and the constant reminder of a return to sixth-form was beginning to become ever present in Kyle�s thoughts. It had been the best seven weeks ever as far as Kyle was concerned, a new found sense of freedom had clashed head on with the making of a new � and now probably best � friend, Chris Deaton. Chris, unlike Kyle, was outgoing, adventurous, and unquestionably �cool�.�

These thoughts released a sudden feeling of guilt, as Kyle began to slowly reconstruct the events of the previous night in his mind. The skate park before cheap alcohol and an empty house resulted in makeup, lingerie and Kyle�s first sexual experience. His stomach began to ache with guilt. As the pair�s intoxicated conversation lead inevitably towards the topic of girls and sex, Chris had opened up about what he called his �lesbian sex fantasy�.�

�It�s not just watching�, Chris explained �yeh, that�s alright � it has a time and a place - but I mean active participation. And not like, oh here�s the dude that comes along and ruins the scene. I fucking hate when that happens in porn flicks�

�Yeh, me too. It�s a damn shame when that happens� Chris replied, unsure of what his friend was getting at.
�Exactly. It�s just the masculinity � and they�re always so fucking macho � that just ruins such a moment of feminine beauty. And that�s what I mean. I want to part of that moment.�

�But isn�t that a catch-22 situation? You can never participate without breaking that moment��

Chris grinned, �Well yeh, and this is the bit that nobody ever talks about. The ultimate lesbian sex fantasy is to accept that, and embrace some kind of femininity�

�I don�t follow. Light some candles and play some Adele while you get stuck in?�
Laughing Chris replied, �Stuck in? No. I mean to be one of the girls in the scene. Kind of like an outer body experience�

�You�re mad, how is that possible?�

�Well, I don�t know, it�s not. But it is, kinda. If I looked and acted like a girl, in that particular situation, that is active participation�

Kyle at this point began to question whether or not this was a joke, but Chris continued. �It�s not the idea of a cock being involved that turns me off. Everyone loves a blowjob video. It�s the macho, ultra-masculinity which ruins such a beautiful moment. And all I�m saying is, if I looked feminine in this particular moment, then that would be my ultimate lesbian sex fantasy�

�So you want to look like a girl while having sex with a girl?�

�Why not? It�s like an extension of that sexual desire��

�It�s narcissism gone mad, that�s what it is. But men in drag look terrible, they look like exactly that � men in drag.� Kyle�s mind repulsed at the thought.

�Not necessarily. You�d be surprised. Right check this out, and don�t act all freaked out�, Chris then proceeded to open up some Youtube videos on his laptop. �That, right, is Bailey Jay. She�s hot yeh?�

�Obviously.� Kyle responded, unsure of the purpose of showing him this clip.

�Well, she is a dude. Or at least, she used to be.�

�Fuck off. No Way� sniggered his friend

�Yep. Here�s the proof�, loading up a separate window Chris typed in the address of a porn website and clicked through a few pages. A video loaded up of the same girl in the Youtube video, now accompanied by another with blonde hair, both with exposed cleavage. �Ok so let�s fast forward a bit. The other one�s�
called Bee Armitage�.

�How do you know all this?�

�Well, just look.� The video jumped to 20 minutes in: Bee wearing stockings and a bra pulled down to reveal small breasts, Bailey completely naked, her smooth white skin accentuated by her long dark brown hair. The hand of each girl gripped the other�s fully erect penis.

�What. The. Fuck.� Kyle was genuinely shocked.

�I know, weird isn�t it?��

�Why? Why do you know about this, and why are you showing me?� Throughout his protest, however Kyle�s eyes were glued to the screen, as Bailey began to suck the blonde haired girl�s 8 inch cock. �You�ve got a big dick for girl!� she giggled. �This is fucking wrong�, Kyle backed away from the computer desk with the familiar stirrings of an erection beginning to form. �My penis is just confused, they look like girls� he thought, trying to justify his reaction.

�Well, yeh so that�s what I kind of mean� Chris broke the silence, and closed the internet window.

�That you want to be some kind of tranny?� Kyle accused.

�Don�t be so fucking lame. It�s just an idea. It doesn�t repulse me, what did you think?� he asked.

�I don�t know man. It�s a mind-fuck. They look so feminine. It�s probably just the tits, all that surgery�

�Not necessarily, there�s girls that haven�t had any, and there just as hot�, he replied.

�Why do you know all this? How much are you actually into it?�

Chris was reluctant, but perhaps spurred on by the amount of alcohol which he had consumed, he decided to open up to his friend. �Look, you�re my friend right? We�ve opened up about loads of shit. I didn�t judge you when you told me about painting model planes or having a crush on my sister ��

� � that�s completely different� Kyle interrupted.

�Ok yeh, fair enough. But. Well� I�ve tried it� Chris nervously confessed.

�Tried what?� Kyle�s face had remained in a state of disbelief, confusion and shock.

�The girl thing. Like dressing up� he continued.

�Man, this is weird. I don�t think you should be telling me this.�

�Oh, stop acting like some narrow-minded idiot.� Chris angrily replied.

�I�m not. Okay. How have you tried it?�

�I�ve tried on some of Jodie�s things.� Kyle nervously looked around the room, unsure of how to respond. Eventually he asked, �And?�

�It�s different. It�s kinda fun, just because it�s so out of the ordinary. You should try everything once, right? And experience as many different things as possible. Life is for living, and if you want to try something, man, then you should just do it. It�s just an idea � the lesbian sex fantasy � that spurred it on, and well, I acted on it. Because why not?� He continued to rant in excuse of his confession.

�Yeh, I guess so.��

This had been Chris�s philosophy ever since the two became friends, and perhaps one of the things Kyle found so endearing about him. His outgoing, confident nature was infectious, and Kyle couldn�t deny that this had, in some way, rubbed off on him. The development of his own personality in the last 7�
weeks wasn�t simply coincidence.�

�So what did you wear?� Kyle asked.

Dresses. Stockings. Underwear. It sounds weird, but Jodie has a lot of sexy lingerie�

�I bet she does!� Kyle�s thoughts wandered to thoughts of his friend�s sister. Jodie was two years older than the boys; mature, sexy and independent. Kyle had more than a small crush on her. �Let me see them�, he asked.

�That�s a bit weird isn�t it? Throwing round her knickers like they�re porn mags.��

�You�re the one who�s been trying them on, come on, I�ve always wondered what she�s got on underneath that smart office attire� said Kyle.

�Dude, that�s my sister� he replied, �right okay, on one condition, we try some on. Both of us.�

Kyle laughed and responded �No way. That�s your thing, not mine�.

�How do you know? I thought you shared my philosophy on life. You should try everything, just for the kick of trying it. I thought you were cool!� Chris firmly played the guilt card.

�Hmmm.� The tactic had clearly worked.

�Right drink the rest of this. Then we do it. Who cares, nobody will know, it�s just you and me.�

The pair consumed the rest of the alcohol they had managed to acquire for the night and preceded into Jodie�s bedroom. Her room, unlike Chris�s, was tidy, well-furnished and perfumed. Opening her bottom draw revealed an assortment of lace and satin. From pink to leopard print, the array of different types, styles and patterns was extensive.�

�This is where she keeps the good stuff� Chris explained.

Both boys then began to rummage through the garments, selecting items which they deemed particularly sexy. Selecting a leopard print bra, thong and matching garter belt, Chris placed his choice on his sister�s bed. Kyle eventually decided on a pink set with lace trim finished off by large bows at the front.�

�Nice. A very girly choice� Chris laughed.

�Fuck off. They�re all pretty fucking girly� Kyle responded.

�I know. I know. I�m just fucking with you. Don�t get my sister�s knickers in a twist� Chris joked as both boys began to laugh.

�Okay, bit more alcohol �my dad has some he never touches downstairs � then we do it.�

After half a mug each of a strong tasting liqueur both boys shuddered and began to feel heavily intoxicated. Chris began to undress, removing his t-shirt revealing his hairless, slim, slightly toned body.�

�That reminds me� Chris started, �You�re not hairy chested, right?�

�Ermm. No, why?�

�Well it spoils the illusion if it�s not done properly�

'I guess�, Kyle somewhat reluctantly answered.

�So, you�ve got to commit to legs too�.�

Kyle eventually agreed to shave the hair from his legs in the hope of showing willingness and an open-mind to his friend. �If we�re doing this, I�m not going to chicken out now� he thought. Chris then lead him through to the bathroom and helped in shaving what little hair covered his slim legs before tackling his own.�

Back in Jodie�s bedroom, Chris decided to dress first. This, he thought, allowed him to help his friend, while at the same time making him less self-conscious. Turning his back to his friend, he unbuckled his jeans, letting them slide to the floor, before stepping out of his underwear. Kyle, not knowing whether to look or not, decided to sneak half-glances at what the other boy was doing. Pulling on the thong first, Kyle couldn�t help but check out the way his bottom fit perfectly into the underwear. �From behind, that could be Jodie� he thought. Chris continued to roll up stockings and attach them to the matching garter set before finally hooking up the bra. �He�s done this more than once� Kyle noticed. �Right, ok your turn, what do you think?�, he turned round and twirled for the other boy. �You look like your sister� was all Kyle could respond. �Okay� lets do you?� Chris answered.

Five minutes later both boys were sat on the carpeted bedroom floor, while Chris using a vanity mirror began applying foundation, mascara, eye-liner and lip-gloss before styling his already long hair into a more feminine style. Sitting in the skimpy underwear set, with his now smooth legs against the stocking material, Kyle couldn�t help but feel some stirring beneath the pink panties he wore.�

�This is the strangest thing we have ever done�, he stated.

�Yuh, I guess�, Chris half answered, too busy applying a delicate line of eye-liner.�

-

�I�m never drinking again� Kyle thought, his recollection of last night�s events overwhelming his sense of guilt and anxiety. The kiss had sparked a feeling of ecstasy which he had never felt before. His body began to burn with desire and passion as Chris�s hands explored his shoulders, bottom and eventually the front of his pink bowed knickers. His penis strained against the satin fabric with a strength he had never felt before, and his own fingers began exploring the smooth legs wrapped around his own. Fuelled by desire and alcohol, his hand moved up towards the huge bulge bursting out of the leopard print thong. Moving up and down the thick shaft, he could feel his own orgasm beginning to grow. Moving the satin panties to one side, Chris grabbed the other boy�s penis in his hand and began to slowly masturbate it. Following his lead, Kyle returned the favour by releasing the throbbing length he had been massaging from its silky constraints. As their penises began to rub against one another, the unstoppable urge to have his eachother became uncontrollable, and images of Bailey and Bee raced through each pantie-clad boy�s head.�

�I want you Kylie�, Chris murmured.�

�Kylie?� Kyle responded confused, the moment suddenly clashing with reality.�

�We shouldn�t be doing this� he said through heavy breathing. Kyle�s orgasm erupted, spurt after spurt of thick cream covering the hands, panties and stomach of his partner.

�I�� he mummered. �We shouldn�t have� I� You� I�ve got to go�

He stood quickly, feeling dizzy and lightheaded. Reaching for the pile of his regular clothes, he quickly dressed, putting his clothes on over Jodie�s lingerie in haste. Quickly making for the door Kyle exited without another word. Chris lay on the floor covered in his partner�s still warm sperm, his own erect penis standing firmly from the side of the leopard print thong.



Comments welcome.�
No grammar police though please.�
More to come if enough positive feedback.

This story archived at http://tgfiction.net/viewstory.php?sid=255