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Date: Sat, 30 Dec 2000 22:50:07 -0600
From: Apollo
Subject: Naughty or Nice (Santa) TG
WARNING: The following creative artwork includes topics of voluntary sex,
crossdressing, and other themes. If you find this sort of material
objectionable, then press the back button on your browser. My original
story may be copied, reproduced, downloaded, and otherwise shared without
restriction. Enjoy!
Written by: Apollo (anonymous)
Naughty or Nice
I was working as the shopping mall Santa Claus, hey, it was a job,
y'know? Besides, what else would I be doing on Friday nights and the weekend,
my girlfriend and I had just broken up and I wasn't in the best of moods. The mall
hired a couple of Santa's helpers' and dressed them up as elves. To avoid any
lawsuits, they hired some women and some men -equal opportunity elves. The
elf uniform was basically a green teddy, with enough extra material to make it
look presentable in public, green tights or stockings, and platform heels. All
capped with a green cap. One afternoon after a particularly boring day my eyes
started to wander during my break. I was surprised that one of the elves had
such a tight butt. Small breasts I noticed, but enough to say there was breasts.
The uniform fit so tight. The long blonde hair flowing down the back almost to
her ass. I was starting to get a good boner. Then it hit me as the elf turned
around completely. It wasn't a she, it was a he. I had never had anything but
straight sex in my life, I was surprised at my reaction to him, er, her. Whatever.
S/he looked cute.
I shook it off and went back to work. I found out later that his name was
Jess and he had just started to work that day. Out of curiousity more than lust I
brought up a conversation with him in the dressing room, just talking junk about
the weather and the crowds and the stupid shoppers. His clothing was just a
shirt and jeans, you couldn't tell anything except he was a guy. He pulled his
hair into a pony tail and looked like half the guys in my old high school class. I
thought I caught his eyes drifting to my boxers as I changed clothes, it made me
feel good but funny at the same time. I decided that there was nothing to lose,
so I invited him out for a beer later that night at the local watering hole.
We had several drinks and were feeling pretty good. I was actually
enjoying Jess's company, he listened and was in to what I was talking about. I
couldn't help my eyes drifting to his chest looking to see any signs of the breasts
I thought I saw earlier in the day, and I think he must have sensed it. I also
thought he was checking out every guy who walked by with a tight ass, but it
might just have been my imagination. Anyway, the bar was closing. Jess
suggested we pick up a bottle and go back to his apartment to continue our
drinking marathon. Hey, no work or school tomorrow, I wouldn't mind getting a
little more blitzed.
We walked into his place and cracked open the bottle. I started to tease
him about only being Santa's helper while I was the he-man, King of the Hill,
Santa Claus himself. Jess said he thought my costume would be too hot, but he
really liked the elf suit. Somehow I talked him into trying it on then and there, so
he did. S(he) came out and my mind froze. Somehow her tits were much larger,
I don't know if he had been holding them in or had stuffed them, but they were
very noticable against the skin tight green suit. The ass jutted out too, I don't
know if there was padding or if I had just not noticed it before. The long blonde
hair caressed her shoulders, and she had put on eye makeup. She also had
green lipstick and green fingernail polish on, something she did not normally
wear in the mall. I joked that no guy in their right mind would kiss a girl with
green lips, she flipped the hair back and blinked her eyes at me, said, "wanta
bet?". With that she walked the final few feet over to me, stood on her tiptoes
and laid a really good kiss on me. It blew my mind, here I am a straight guy,
never been with another guy before except in football games, and now I'm letting
some guy dress like a gal kiss me. And I liked it! Next thing I know I'm being
French-kissed, and I'm starting to kiss back. Her arms go around my neck,
pulling me in, I reach out toward her and she shifts to the side so my hands end
up on her boobs. I'm not sure what she had under the bra, but it felt good. I
move my hands over to her butt, she started to grind into my cock. She slips
down onto her knees and takes out my cock. I'm just staring as she starts to
playfully lick it. She asks me if I like it, I say yessiree, and he deep throats me.
Pumping and licking, she brings me to the edge of explosion and stops. I am
gasping for air as he turns around to show me where the tights and the costume
had a slight tear. I know what he wants, I shove my cock into his male cunt
which was well greased and wide open, apparently Jessie had spent some time
with a dildo in the past. I start to move into him, back and forth, in and out, she
starts to groan and moan. That puts me over the edge, I flood his male cunt with
sperm that just spills out as I pull out. I didn't know what I should be thinking of, I
knew that she was really a he, but right then and there it didn't matter. I didn't
stay around too long, but the next day at work seemed strange, at least at first.
We got over it and were laughing up a storm as the week went on.
The next night off we decided to go drinking again, but this time we ended
up bringing the bottle back to my place. More small talk, then somehow he
convinced me to model the Santa suit. While I was putting on the padding and
red suit, Jess said he had to go to the bathroom for a moment, so I didn't think
anything of it. When I came out into the living room I looked around, no Jess, so
I just sat in the reclining chair. Then Jess came out - he had gotten dressed
himself, but it wasn't an elf costume. He was wearing knee high socks, Mary
Jane shoes, a plaid skirt that was too short, a white blouse that buttoned down
the front, and he had his hair in two pigtails. He had put on a little makeup, not
much, but he - I mean she - looked like the Catholic high school girl. Jessie
walked over and sat on my lap, then proceeded to give me a lap dance, all the
while talking like a little kid. She wanted a Barbie and Ken for Christmas, so she
could have them make out together...she wanted some sexy grownup clothes,
she wanted a boyfriend, etc. I asked her if she had been naughty or nice this
year. She then sat closer to me and whispered in my ear that she had been a
bad girl, and was very good at it. She opened her blouse and I could see small
but natural tits, as if she was on hormones or something. I started to suck on
them and he really got into my paying attention to him. He stands up, faces
away from me, bends over and grabs his ankles, with the skirt riding up over his
panty-less ass. I unbutton my pants and take out my cock. Jessie cries out that
she wants me really bad, so I give in and fuck her hard. We take a break, but
then she sits on my dick in the chair, riding up and down crying out give it to me
Santa Claus. How could I resist?
This was getting to be a habit, one that I never thought I would be me, but
I was drawn to Jessie. I know that she is really a he, but he acts and looks like a
she. The next night off we decided to go to my place and she brought over the
elf suit. So I put on the Santa suit. I wasn't sure which game she wanted to
play. Turns out that the elf wants to give Santa a Christmas present - the best
blowjob of them all. Jessie brought a new meaning to the term Happy Holidays.
Being in the mall we generally had time to kill during lunches, hey it
doesn't take an hour to munch down on a burger, so Jessie and I just through on
some sweats and walked the mall. We went into the lingerie shop, the girls
behind the counter didn't know anything, they just assumed we were shopping
for our girlfriends. I picked up some racy lingerie and watched Jessie's face turn
red. I put a padded bra up against his sweatshirt and all the girls laughed. They
didn't know that I had plans for some of that lingerie. Jessie just kept whispering
if we could leave now, get out of here, but I told him that I expected a properly
outfitted young lady tonight when I came over. I finally bought a black bra with
open tits, hot pink crotchless panties, and red fishnet stockings. Jessie
complained that they did not match, but I told him to model them for me tonight
anyway. I also told Jessie what else to wear from his regular girl clothes closet.
I showed up on time with a bottle of wine. Jessie came out of the
bedroom all dress up for me, exactly as I described. She wore a pair of white
hot pants and the pink panties showed through. She wore a white button down
blouse that the black bra showed through. The deep red fishnet stockings
matched the fingernails and the lipstick. She looked ridiculous, but was
obviously advertising that she wanted to show off her good parts, and she
wanted to please her man. I told him that he could be a she, I only wanted to
think of him as a her, so after giving me a blow job I made her turn around as
she dropped her shorts. I put my cock into her she male ass and pumped for all
it was worth. She complained that she looked like a whore, I said she was my
slut. She enjoyed the sex, almost as much as I did.
Christmas came and went, and both of us were out job hunting again.
However, the mall was so happy with everyone - we were a lot better than last
year's drunk Santa- that they told us we were wanted back next year. The mall
management also said something about having a skit next year for Halloween,
like a costume extravaganza in the mall with us modelling the costumes for all
the customers to see. I could hardly wait to see what costumes Jessie and I
picked out...