tagIllustratedShemale Tales: The Christmas Party

Shemale Tales: The Christmas Party

bysilkstockingslover©

Summary: Young woman discovers the perfect man... a woman with a dick.

Note 1: This is a Christmas 2016 Contest Story so please vote.

Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing.



Shemale Tales: The Christmas Party

I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christmas party. I'd only warmed up to a few people, and the only one I would consider a friend was Jamie (if ten days of working together constituted a friendship... and based on our frank discussions about sex and relationships, I would say it did). Yet having moved here only six months ago and hoping to stick around after the Christmas season (so far this was only a temporary job), I figured I should attend and make a good impression. Show willingness and all that.

Plus, my supervisor had said I could bring my boyfriend... Michael being the only reason I was still in Los Angeles. I had come to start an acting career, but so far had only gotten a job as a waitress at a dingy restaurant and now this temp help job. In pursuit of my so-called acting career, I'd only gotten three audition call backs, and they'd all turned out to be false hopes.

Plus, the party was going to be in the same building as the firm, so I wouldn't even have to leave and come back... my tiny apartment being a good hour plus drive.

Jamie asked, in her usual blunt way, "Is that what you are wearing tonight?"

"I was before you asked 'Is that what you're wearing tonight,' in that revolted, condescending tone," I replied, instantly self-conscious. "Do I look that bad?"



"It's a formal Christmas party with hints of sexy," Jamie pointed out.

"Oh," I replied, disappointed. The idea of going all the way home to get dressed up and coming back was a definite bummer. "I guess I'd better skip it. My sexy clothes are a long way from here."

Jamie suggested, "Tell you what: come back to my place after work and I'll dress you in something utterly fuckable."

"Michael would like that," I approved, it being a good two weeks since we'd had sex. He'd been gone all this week, and I'd had my period the week before. I'd blown him twice during that first week, but my kitty hadn't purred for what seemed like an eternity! I was used to getting it every day or two.

"Everyone would like that," Jamie elaborated with a wicked smile and a naughty tone.

I laughed, "Am I that boring?"

"You could add a little spice to your wardrobe," she pointed out. Truth was I dressed sexy underneath my conservative attire, but in my outer garb I was trying to look professional for work... a job I was hoping to keep even after the Christmas rush was over. It didn't pay a whole lot, but office work certainly beat running around a café delivering burgers and fries that could be called 'deluxe' just because they were served on plates and the ketchup was in actual bottles.

I justified to myself, 'At least I'm wearing thigh highs beneath this conservative attire since Michael likes them and I was hoping to get laid tonight'. But instead of giving away my defensiveness I nodded, as I admired her young, hip outfit, "I suppose."



"Trust me," she smiled. "You'll look fucking unbelievable."

"And unbelievably fuckable?" I questioned wickedly, horny from these two weeks without any action... which was an eternity for me. Although I looked nerdy on the outside, deep down I was somewhat of a nymphomaniac.

"Guaranteed," she nodded, giving me a wink before heading back to work.

By four-thirty we were at her flat, both starting our second glass of wine, and in her bedroom looking through her closet.

"Get undressed," she ordered.

I laughed, "I'm not that easy, you philanderer. No dinner first?"

"Dinner is after," she smiled back.

So I took off my clothes, quite comfortable with my body, leaving on my bra, panties and thigh highs.

"Thigh highs," she acknowledged, looking my body over. "Nice! Aren't you full of surprises?"



"Michael likes them," I explained.

"So do I," she smiled, lifting up her skirt to show me she was wearing them too.

"Great girls think alike," I smiled.

"Indeed," she nodded, giving me a second look just like a guy often does.

She went to her closet and brought me a dress. "Try this on, but you'll have to remove your bra."

"Really?" I asked, as I grabbed the dress.

"Really, really," she responded playfully.

So I took off my bra and slipped on the tight black dress. It was so tight it made my hardening nipples poke through, making me self-consciously cross my arms to hide them.



"Don't hide your tits." Jamie scolded.

"You can see my nipples," I pointed out, mentally realizing the pun.

"So what?" she shrugged. "Every mammal and marsupial in the world has nipples."

I laughed, "I guess so."

"And you need black stockings for a black dress," she added, going to a dresser drawer and coming back with nylons.

I took them and started draping on a stocking. These were nice! She asked, "So is Michael the one?"

"I don't know," I shrugged. "I mean he has a job and isn't too much of an asshole, so he's an upgrade from my last dozen boyfriends."

"Maybe you should try girls," she teased, a joke she'd made fairly often during the past few days while Michael was gone.

"I told you I like cock better than cunt," I responded, having tried both.

"Maybe you need a she-male," she joked.

"That's exactly what I need," I agreed with a chuckle. "I love tits, I love ass and I love cock. A beautiful she-male would be the best of both worlds."

"You mean you love cock in your ass," she teased, making me once again regret telling her I enjoyed anal sex and that my biggest fantasy was to be double penetrated.

"I knew I shouldn't have told you that," I said.

"What? I told you I love anal play too," she reminded me.

"Yes, we're just two anal sluts," I joked, as I finished smoothing out the second stocking.

"Speak for yourself," she protested. "I'm a perfect lady... just one that loves to fuck."

"Well, then I'm a lady too," I declared.

"Yes, ma'am, you are. Now pose like a slut for me," she said, finishing her second glass of wine. "Pretend Michael is walking into the room."

Enjoying the female companionship, being rather lonely since my move, I did. Plus, Jamie reminded me of my college friend Barbara, who'd always brought out the naughty in me. My first lesbian experience, my first threesome, and my first fisting were all with her, she being imaginatively generous with her hands and tongue.



"Very nice," she approved.

"Sure, if I was staying at home to seduce Michael. But for a staff Christmas party this is a bit much," I pointed out... just like my nipples pointed, quite visible through the dress.

"I guess," she shrugged, as she went and grabbed another dress.

"Really?" I asked, this one even shorter.

"It will hide your nipples," Jamie pointed out.

"Fine, I'll try it," I said, changing dresses.

As I did, she asked, "So in a perfect world you would be with a shemale?"

"In a perfect world, sure," I nodded. "Man drama is exhausting. Conversation with men is non-existent."

"So shemales are perfect for you," she said.

"Sure," I laughed.

"I'm serious," she continued. "They have a dick, they have tits, and hopefully they can hold up their end of a conversation."

"Sure," I agreed, "find me a shemale and my life will be perfect."

To my surprise she didn't respond to that.

After a pause, she agreed, "Okay, that one may be too short. That was my nun's costume from last Halloween."

"You were a nun for Halloween?" I questioned. Duh silly, she'd just said so.

"Yes, I went around blessing the sinful," she smiled wickedly.

I laughed, "Now that I can imagine." I then added, "Do I make a sexy nun?"



She nodded, "Sweet and sexy... a perfect mixture."

"I may have to borrow this for next Halloween," I said.

"Or church on Sunday," she quipped.

I roared with laughter as I posed playfully. "Father, I have sinned...."



"Suck two cocks, take a double penetration and two loads of the Lord's seed all over your face, my child," Jamie mocked.

"Is that all?" I asked, trying not to erupt with laugter.

"And three 'Oh God's as you come, my child," Jamie said, as she walked to me and said, doing the hand motions, "In the name of the Father and the Son and the Holy Cock, amen."

"Now I feel like I have to do that," I joked.

"Then do it," Jamie shrugged.

"All I need is another man," I said. Michael, like most guys, was likely to go along with it at the drop of a hat. Or better, at the drop of a thong.

"Or you could include a shemale," she pointed out.

"Well, that goes without saying," I laughed, before adding, "as long as she has a big dick."

"And a nice rack," Jamie added, cupping her own tits under her outfit.

"Again, without saying," I agreed, playing along.

"Okay, I think I know the perfect dress for you. It's both classy and sexy," she decided, as she went to and from her closet once again, and added, "it even matches your original stockings."

I put on the dress and returned to my original stockings, and she added, "Besides being classy and sexy, it showcases your tits, your legs, and has quick access to that sweet peach of yours."

"Sweet peach?" I questioned.

"Do you prefer cunt?"

"When I'm being a proper lady, even peach is a bit racy, but when I'm getting fucked, I far prefer cunt. I even get off on being called a slut or a cunt," I answered, liking nasty talk during sex. I was perceived as sweet and innocent on the outside, but I was a kinky slut underneath and liked to be used as such. I was feeling a bit competitive with this self-assured woman and was trying to shock her with my bold revelations.

"You like being treated as a slut, don't you?" she asked conversationally, not shocked in the least, as I changed dresses.

"Guilty as charged," I said, putting my hands out as if to get handcuffed, raising the bar.

She smiled, "I have a pair," raising it back.

"Not without buying me dinner first," I joked.

"Or whipping out my big dick," she quipped.

"Yes, because dick can be an excellent dinner," I quipped right back, enjoying the banter.

"Yes, it can be a full meal deal," she agreed, as she studied my body in the dress.

"So?" I asked, posing for her.

"Perfect," she nodded.



"I know I am," I responded playfully.

"You certainly are," she smiled back, making me feel good about myself. That had actually sounded sincere!

We each had one more glass of wine and took a taxi back to the office.

While we were waiting for the taxi, Michael texted me, saying he was already there. I apoligized for being late, but promised it would be worth the wait.

Jamie gave me a long, admiring look, top to toe, and said, as we entered the building, "You actually do look unbelievably fuckable," quoting my playful phrase from earlier.

"As do you," I replied back, surprised that she'd worn a rather conservative outfit, except that it was short enough to show off the lacy tops of her thigh highs.

"I always do," she joked.

"Yes actually, you do," I laughed at her self-centered personality. Somehow with her, self-centered worked. She looked good and she knew it, but that didn't stop her from making me feel just as beautiful.

As we walked into a large, elegant, banquet room, oil paintings on the wall, luxurious furniture grouped around the edges of the room and a huge long dining table in the middle, set with the very best china and silver, Jamie ignored all this sumptiousness as if it were nothing, and just continued our conversation, adding, "Although when push comes to shove, so to speak, I prefer to do the fucking."

Before I could break my attention away from the furnishings and respond to that intriguing statement, Michael walked over to us and approved, "Wow, you were right. It was worth the wait."

I slyly moved my hand and gave his cock a squeeze, "Wait a little longer and I'll show you just how naughty I can be."



"Oh, God," he groaned, before adding, "You sure we can't go home right now?"

"You be a good boy for me now, and later I'll be a very bad girl for you," I purred, a promise I planned to keep.

"What's gotten into you?" he asked.

"Not you," I complained, just before my supervisor Brooklyn showed up and introduced herself.

"Who's the handsome young man?" she asked. She was dressed in a short skirt, a frilly blouse showing lots of cleavage and had her hair in pigtails as if she were trying to look ten years younger than she was.

"My boyfriend Michael," I answered, before adding, "And Michael, this darling lady is my supervisor, Brooklyn."

They exchanged pleasantries, then we headed to our table for a few generic Christmas greetings and company updates before dinner was served... which was easily the best meal I'd ever had... like in ever.

During the dinner I slyly rubbed Michael's cock under the tablecloth... wanting him horny as hell so he would want to get out of here as soon as dessert was served, so I could get my own dessert back home. I should note that, unlike many girls, I not only loved sucking cock, but I even loved the taste of cum. I would sometimes just suck and swallow for a snack... like I said, I was a lot dirtier than my outer ladylike appearance gave away... like many women I suppose, since society wants us prim and proper in the public's eye, but a slut in the bedroom.

Suddenly Jamie came up behind me as I was still seated. She had been sitting across from me during dinner, placed her hands rather possessively on my bare shoulders and caressing them teasingly asked, "Are you ready for things to get interesting?"

"Always," I smiled, even though I had no idea what she meant.

She smiled, "No, I mean really interesting."

"Ah... sure," I said, although her tone was confusing. Surely she knew I wanted to get Michael home and in bed as soon as I could. "But first, I really, really need to pee; the fourth and fifth glasses of wine are running right through me."

As I approached the door, Jamie called out, "Be careful in there."

"Um, okay," I said, thinking she was acting really weird, but figured she was just already pretty drunk like I was.

I headed to the washroom at the far end of the hallway, thinking the fifth glass of wine may have been a mistake... realizing I was much more tipsy than I'd thought... although wine also made me extremely horny and adventurous.

I walked into the washroom planning on telling Michael we were leaving as soon as I returned... I needed to swallow a load of cum and then get fucked hard... when I walked into my first of several shocks of the evening.

A blonde secretary in crotchless panyhose whose name I couldn't remember... it started with an 'A' I think... was being fingered by one of the partners of the firm, Mrs. White... as the blonde moaned, "Oh yes, I'm so wet."



I stared for a minute, as Mrs. White asked, "You want to get fucked, my little slut?"

"God, yes," the blonde moaned.

Mrs. White turned her head around and looked me straight in the eye with a smile and asked, "Want to come and join us, Jill?"

The blonde looked up hoping I'd accept, not the least bit embarrassed to be caught in such a compromising position as I stammered, "N-n-no thanks, ma'am," and scurried out of there.

As I closed the door, the secretary begged, having already forgotten about me, "Please fuck me, Mrs, White."

Once in the hallway, I shook my head... that was crazy! It was also kind of hot... although I was in no way a lesbian. I mean I found women pretty... and sexy... but I liked cock... my few times eating pussy convincing me I wasn't really bi... although I would do it when I was sufficiently drunk or to please a voyeuristic guy.

As my thoughts wandered, I worried that I might pee my panties and decided to use the stairs to walk up the three flights to my office and pee there.

I got to the washroom and barely made it. As I went pee I sat there for a few minutes replaying what I'd just witnesed. I'd seen two girls in the act only one time that hadn't included me, and that was at a college party... but at work? That was crazy. It was then I recalled Jamie asking, 'Are you ready for things to get interesting?'

And then she'd warned, 'Be careful in there' when I headed for the washroom.

Did she know what was happening in the washroom?

I wanted to text her, but had left my phone back at the table.

Oddly, the brief lesbian act had only enhanced my horniness, and as soon as I retrieved my phone I was going to grab Michael, hail a taxi (unless he was sober enough to drive) and we were going to have a marathon fuck session... with a probable appetizer of can't-wait-that-long blowing him in the taxi before we arrived home.

I went to my desk and downed my last half a bottle of water before I headed back downstairs, it now being a good fifteen minutes since I'd left... Michael most likely wondering where I was. I walked down the hallway, surprised to see that no one was around, and that the ballroom door was closed with Jeremy, the mailboy, standing guard. His clothes were rumpled and his shirttails were hanging halfway out of his slacks; he'd dressed in a hurry. Right after a formal dinner?

Reaching him, I asked, "May I go in?"

"Sure, Jill," he agreed, opening the door for me and bowing with awkward formality to invite me in, "Have fun!"

The way he said that was ominous and I learned why a few seconds later as I entered the banquet room and got the shock of my life.

I had just walked into an full scale orgy! Half-dressed or naked people were having sex all over the room! At just first glance, I noticed couples, threesomes, foursomes, daisy chains... just about any combinations you can imagine!

I stared, paralyzed, as Jeremy closed the door securely behind me. All this had sprouted from a formal dinner in fifteen minutes?!

To my right was more lesbian sex; a brunette I didn't recognize was leaning back on an elegant upholstered divan, being eaten out by a blonde, girlfriend to Jerry, one of the interns. A quick scan of the immediate vicinity gave me no sign of Jerry.

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