For four years running Jerry liked to make himself over on
Christmas break and send out a cutesy anonymous photo to all the other fellas
who couldn’t go home for the holidays. It
was his own way to celebrate his inner feminine side that he knew would never
get to see the light of day while simultaneously giving many guys a happy Christmas
gift. Jerry already kept his body shaved
smooth for his participation on the swim team so on Christmas Eve he just needed
to make sure he didn’t have any stubble and clean up his legs. Through his time volunteering to help the
school’s theater group he had access to the best makeup and had learned how to
apply it over the years to really hide his masculinity away. What would look simple to most of the guys he
sent this too was really quite detailed, what with the foundation, subtle
blush, lipstick, lip gloss, eye shadow, eye liner, and eyelash extending
mascara. Even the painted fingernails
added to the glamour.
Jerry loved hearing the guys over the next couple weeks try
to guess where this mysterious ‘Jenny’ was.
He always made sure to pose with just enough of his dorm room showing
that it could be identified as from this school, but had extra curtains, and
other decoys to throw off everybody’s trail.
This year he even included an old ironing board and a festive, if small,
Christmas tree. The pièce de résistance
this year was the hat. Before, he’d
always used long overly feminine wigs but this year his hair was cut too short to
weave a wig into, so he got this wintery Santa-like hat and glued some cute
bangs coming out the front and a cute braided ponytail coming out the
back. The pose this year would be a
little more risqué as he wanted to do a ‘Nude Jenny’ photo as this was his last
year. So with the camera facing him on
it’s little tripod and the screen flipped up he sat down and moved until the
pose was perfect. His knees could hide his
flat chest and everybody’s imagination would let them see breasts there. His legs held close together would hide his crotch
away and even this position would give the hint of a wider hips and rear while
his shoulders pulled in a bit would give the hint of a smaller arms and
shoulders. Setting the camera, looking
up and *CLICK*
Jerry wasted no time in sending the photo out with the
simple silent prayer that everybody would have a happy and safe holiday and
that this would bring them at least a little bit of joy. As he was put the camera away and started
pulling down the decorations, he didn’t realize that the dozens of recipients were
all sending out a similar holiday wish.
Most of them recognized that they’d never meet Jenny but were sending
out silent prayers of their own, wishing Jenny a Merry Christmas and hopes that
she’d get everything she ever wanted. The
holiday spirts, far more ancient than the commercialization of Christmas or
even the birth of the Christ himself, felt this give and take of love and
thanks. They recognized that this love was
based on something Jerry felt he could never have and desired more than anything
else. And most importantly it recognized
that if Jerry got this wish granted, as these university boys all wanted, the
holiday giving would be increased and make everybody happy.
When Jerry stood up, he felt a tingling go up and down is
smooth skin. He just assumed it was the
thrill of helping out others but instead of dying away it intensified. He closes his eyes for the last time in the
middle of pulling his cute robe on. When
Jenny opened her eyes, she let out a sigh of the truly contented. She had the fleeting recognition that she’d
been born a boy and had just been given this wonderful life, but that faded as
she shook her head and let out the braid in her long hair. A
small smile spread over her lips, knowing that the cutesy photos she sent out
every Christmas made the guys so happy and this year’s R rated nudie would be
no exception. She couldn’t wait for
classes to begin so that she could see everybody’s reaction in person. Until then her phone constantly beeping was
signal enough of her success… wishes for a Merry Christmas and thanks for the photo
would keep coming in all night long.
Thank you for another beautiful story with pictures of the lovely Jenny.
ReplyDeleteI hope that your Holidays are at least as beautiful as you.
Hope you had a wonderful Christmas and a great New Year going forward in 2020!
ReplyDeleteYou got your naughty AND nice all in one Christmas caption this year!