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Kylie and Chrissy

The following story is the first part of ‘Kylie and Chrissy’, a story documenting the blossoming sissy-hood of two teenage boys. It is partially autobiographical and partially fiction.


‘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 leaned 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’.

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