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Caitlyn and me
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I've been fascinated by Caitlyn Jenner
since his Vanity Fair cover. I'm not a crossdresser myself although I
sometimes masturbate wearing nothing but my mother-in-law's girdle
but I like looking at crossdressing porn featuring matures like the
fabulous Carollyn Olsen. All the photos I've seen of Carollyn have
been of him fully dressed but that's the way I like it. I love to
fantasise about what he's like under his elegant women's clothing
that he wears so convincingly ; Caitlyn too. I love it that
Caitlyn has undergone breast enhancement – when are we going to see
them ? - but has elected to keep his penis, presumably because
he loves to masturbate it and doesn't want to lose that. I totally
understand and accept guys who want to dress like women but frankly
it turns me off sexually when they look too gawky and masculine. I
like them to look soft and feminine. Caitlyn's photo shoot was a
complete wow that never fails to give me a monster hard on to wank. I
imagine us going on a date, maybe to an upscale restaurant, where no
one suspects anything ; what they see is a beautiful woman and
the maître d' can't be gallant enough. Caitlyn and I share our
private joke and he flirts with me openly and dips his cleavage my
way so that I get horny as hell right there at the table. If I reach
under the table, I can get my hand as far as his knee but no higher
which drives me nuts. He slaps away my hand and tells me to behave,
just like a woman would. Because he is so feminine. All his little
gestures and expressions and the way he tosses his head are exactly
those of a real woman and I find I'm treating him with the same
deference as I would a woman. When we leave the restaurant, he tells
me his family is expecting him home but when he sees the look of
disappointment on my face he leans over and kisses my cheek and says
we can park above the beach for a bit. His mouth is deliciously soft
to kiss and he tongues me enthusiastically while I slide my hand
under his skirt. I ease the elastic of his panties to one side and
liberate his cock. It's a big, a real handful, and he breathes
heavily while I wank him and we continue necking. He's got his skirt
pulled up so that he won't soil his skirt when he cums and suddenly
it's bang, his jizz is all over my hand and the car seat. It's a
lovely, sticky fucking mess and we're both giggling like kids while I
mop it up. As I drive him home, Caitlyn says the wank had been
terrific but I need to know something to avoid misunderstandings ;
he would never take it up the anus. Somehow, I doubt that. Who'll be
first ?
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Posted on : Apr 12, 2016
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