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Shamilah
12-02-2008, 10:00 PM
As crazy as this may sound,this did happen....
I first started working for Harry immediately out of college.
I have to admit,that although he was older - he was in his early 50s - he dressed very stylishly and kept himself in shape - sort of looked like Jack Scalia.He was married to a beautiful woman named Natalie - who is also
an aerobics instructor,and they had a teenage daughter.
His place was a boutique design firm,and we were always under
pressure to deliver to our clients.
As my alter ego - Cara - i usually went out on Fridays or Saturdays,so it never interfered with work,because I did partly like crazy when Cara was out on the town - you get what I mean - staying up to the wee hours in the morning.The only thing my colleagues ever noticed was that I shaved my entire body,and that my eyebrows were trim,but i guess they never thought much of it.
One time though,there was an annual fetish party that was happening on a wednesday night - and I knew I couldn't miss it for the world,all the trannies,shemales were going to be there for a debaucherous party.
I tried to get the Thursday off,but i wasn't successful,so I thought,what the heck,i'll just suffer the next day.
i wore the sluttiest outfit to the party that night,it was a corset,with a feather boa,tiny latex shorts that only covered half my ass,fishnets and 4 " heels.The party was crazy fun,i drank and partied till like 3 in the morning,and even got lucky - i was picked up by a gorgeous half black,half white model(whom I've seen in magazines) - he brought me back to his place and we had an incredible time.When i finally woke up in his arms,it was almost 6 am,so i left for home,even taking one of his shirts,which i threw over my outfit- didn't want to be seen walking around in the morning
in my slutty outfit while people were heading to work.
When I got home,it was still before 6.30,so I thought I;d have a nap till 8 and rush to work.I fell asleep,still feeling the gorgeous model inside me....
The phone must have been ringing for 20 mins when i finally woke up.
It was Linda from work,and it was already 10.30!Shit!I rushed to the bathroom,wiped off all my makeup,lipstick as fast as I could.
By the time I got to work it was almost 11.15,Linda said that Harry wanted to see me,damned!When i walked into his office,he was obviously furious,because of me,they had nearly missed a shipment to an important client - but they still had managed to work it out eventually.
He told me that he had to fire me - as an example to the other employees unless I had a valid explanation.I didn't know what to say,he repeatedly kept asking me for a reason,but i was too scared to say anything,so he finally said that he had to fire me - without thinking,i started to sob like a girl( i guess i was still Cara mentally),he was very surprised to see me behave in such an effeminate manner.I finally decided to tell him my 'secret',my hands were trembling and my knees were shaking.
The look on his face was surprising,I thought he was initially going to say 'get out of here you queen/queer',but instead he seemed intrigued.
He said that he had previously wondered why i shaved my legs and hands,and that he was also surprised that I was very slim for a guy(i didn't weigh more than 120 lbs).He said he forgave me,but that i wasn't to do that again,and that he would tell the other employees that i had a family matter to attend to,and that i could take the rest of the day off.
I was stunned,and was appreciative of his understanding.We never spoke about it again,and things went back to normal - maybe a little different,i noticed he treated me more gently after that - similar to the other female employees,but obviously not apparent;y.
About 2 months later,the firm was meant to work on a business pitch for a potentially new client.This was usually done by the more senior staff and Harry,so I was obviously surprised when he told he that i was to stay around to help.I had initially thought that i was going to contribute as a junior designer to the project,but after awhile i realized that i was only there to get them coffee,write notes,etc - literally the job of a gal friday - which made me really mad.I felt under utilized.When they were finally done,which was late friday night,everyone left and Harry told me that i had to first clean up the conference room,then help his bring some of the stuff back to his place,mostly presentation boards,etc.
The whole way back to his place,i was fuming,the only thing i said to him was how was i getting back,and he said he'd call me a car service.
when we got to his place,i helped to lug the stuff to his study from his car.
when i was done,i looked for him to get him to call me a car home,when i found him,he was sitting on his couch with a drink in his hand.I was about to speak,but he told me have a drink too - i was still mad,so i said that i wanted to leave,but he insisted,and i finally agreed.
He asked me why i was mad,and i told him that i felt under utilized and that i was treated more as a gal friday rather than a designer - he was utterly shocked when i told him that,he said that ever since the day i told him my secret,he unconciously viewed me as a chick.I was dismayed,i asked that he forget what i told him,but he said that he was intrigued and that he was dying to see me as Cara.I said that maybe i'd invite him out one night when i was out as my female persona - but he said he wanted to see the other me that night itself.I told him he was crazy,that he would wake his wife Natalie up,but then he reminded me(and i was aware but had forgotten) that she and their daughter were away for a week.
I said no,it was so screwed up in my head,this was my boss,i didn't want to embarrass myself,and him laugh at me.But he insisted,he then - out of the blue - took me by my hand - which was such a mind fuck in itself - and led me to Natalie's incredible walk-in closet.My knees were tremblling,and i unintentionally bit my lip in excitement.She had always looked hot,in the way that a rich guy's hot wife always did,very glamorous,sexy and almost
slutty way - they only got away with it because their slutty outfits were made by exclusive designers.
He asked me to take my time,he put on a bath for me and left the bedroom.
I was so excited my head almost exploded,i had a nice warm bath,reshaved
my entire body,except for my 'landing strip',when i got out of the bath my skin felt all warm and soft,so feminine.
I went to her clothes like a crazy woman,everything was beautiful,i found her expensive La Perla black lace and white trim thong and bra,putting them on felt so sexy.Her shoes were a little tight,but only a size smaller than mine,so her Manola Blahnik's worked well on me.
I finally decided on a gorgeous tight white dress,slinky and hugging,which showed off my ass and curves,like the type Jessica Biel wears to award shows,super tight,very low back.
Natalie obviously had an incredible collection of makeup,and even wigs((which surprised me),i was so excited and caught up in my transformation that i had completely forgotten where i was,till i heard Harry's voice right behind me "Are you ready dear?" i had such a shock,i was bent over looking into a mirror,applying lipstick,when he appeared.
I looked at him thru the mirror,and noticed that he was staring at my
pear shaped behind - and when he noticed me looking,he was so embarrassed that he quickly looked away.I smiled and told him to be patient and wait for me in the living room.I felt so empowered and sexy .
When i finally was ready,i walked to the living room, he could obviously hear the clicking of my heels coming towards him,he had dimmed the lights and put on sexy music.
He was sitting on the couch when i walked in,and surprisngly jumped to his feet when he saw me.He had looked stunned,he said that he could not believe that this beautiful woman in front of him was his male employee - I even saw him glance down at my left thigh and leg which was exposed by a really high slit,he said he was surprised at how feminine and toned my legs were.He brought me a glass of champange and asked me to sit next to him.
I noticed some strawberries on a counter and i said that i wanted to get one to put in my glass,i deliberately swayed my hips,sticking my rear out as i walked to get it,and when i turned around, I saw his eyes fixed on my ass thru the tight white dress.He looked at me,and when he saw me smiling,he smiled back,and said that my peachy ass was all the fruit he needed.I giggled and swayed back to him,easing myself seductively on the couch next to him.He couldn;t stop his wandering eyes,all over my body,he said that i filled out the dress better than Natalie did,said although she was hot ,I had more of a latina's ass.I told him i was surprised that she kept wigs,he told me that he had bought them as part of this plan - since he was confident he would see Cara tonight.Naughty devil i thought,but i liked it.
After many glasses of champange,i basically had my head on his shoulder and he had his arms around my waist.I looked up at his handsome face and he smiled,he slid his hands up my bare back,then down till his fingers were at the top of my ass cheeks,he pulled me to him,and we kissed passionately,his hands were all over me,he slid down more and his fingers were in my crack,i wriggled uncontrollably,and he smiled,i could see he liked that.I then unzipped his pants,his cock was stiff and hot in my hands,i gently caressed it,then more aggressively i started to jerk it.He loved it,and started to moan,my lips were on his cock before i knew it,licking and teasing it with my tongue,he grabbed my ass and lifted it till i was on all fours on the couch,my mouth still on his cock.He then lifted the dress away,and exposed my cheeks,he pulled the thong aside and began gently fingering me as I sucked him off,this made me start to moan and wriggle my ass.
Before i knew it,i was riding him,reverse cowgirl on the couch.He was sitting back,and i was on the edge of the couch,moving my up and down on his beautiful cock,his hands on my hips guiding me.Eventually he came hard inside me,fully thrusting himself as he climaxed in my ass.
While still on him,i turned round and we kissed for a very long time,me still wriggling on his exploded cock,my cheeks dripping and sticky.
He the carried me to his room,and made love to me for the whole night.He even gave me a love bite at one point on my inner thigh.
I stayed the weekend with him,and he treated me like a real princess making me breakfast in bed,and loving me all weekend.
On monday morning,when i was about to leave he called me and gave me a surprise,it was a pair of sapphire earings,and a 2 thousand dollar voucher to at a boutique in town - told me to get a few sexy outfits.
When i left,my head was still spinning,did that really happen?I got into the shower and saw the love bite,on my inner thigh,and smiled to my slutty little self,it was real.
After that,i became Harry's secret mistress for almost 2 years,he would always bring me along if he had any out of town trips,or whenever Natalie was away I would stay with him.We were both crazily passionate about each other.He bought me many things and i loved him 'like no other woman could'(according to him).
Unfortunately,we finally were caught by Natalie,she was in complete shock when she discovered it was me - she had thought it was some girl from the office he was sleeping with.She had suspected he was having an affair,so she had cut short a trip and come home to find me on all fours with Harry behind me on their living room rug.I have to admit,that when she realized it was me,she seemed less angry,maybe because she thought it wasn't another woman Harry could leave her for.She did make him fire me,and that was that.
At least that's what I thought so,till Harry showed up at one of the clubs he knew I went to as Cara.
We've been together a few more times since,sometimes 6,7 months go by without seeing each other- who knows when we'll officially stop,but everytime it's fun.I still can;t get over how crazy the whole situation is,but that's life i guess....

Cara

flabbybody
12-03-2008, 02:09 AM
actually Natalie was right. he was having an affair with a girl from the office.

very hot story Cara

Shamilah
12-03-2008, 06:45 AM
Thanks so much Flabby

Thatiger23
12-03-2008, 07:44 AM
wow what a story nice ;)

TransformedBG
12-03-2008, 09:30 AM
Wow that awesome! Wish i was your boss! LOL

Shamilah
12-04-2008, 06:37 AM
wish you were my boss?ha ha,very funny dear

bobjones17
12-04-2008, 09:51 PM
wish you were my boss?ha ha,very funny dear

Nice story. You are a good writer. Oh, and your boss is really lucky. :D

Shamilah
12-08-2008, 05:21 AM
YO have a position you wanna hire me for,Bob?

bobjones17
12-09-2008, 01:59 AM
YO have a position you wanna hire me for,Bob?

Lol, I'm a student, sorry to disappoint. Maybe in a few years or maybe you'll be hiring me... :wink:

Shamilah
02-16-2009, 08:33 AM
What are you a student of hun?

bobjones17
03-05-2009, 02:17 AM
What are you a student of hun?

Geography

Shamilah
03-05-2009, 06:03 AM
geography of a trannie's body?

bobjones17
03-06-2009, 04:26 AM
geography of a trannie's body?

You got it. I love the peaks just below the shoulders...

Shamilah
03-17-2009, 06:27 AM
The peaks?what about the mounds at the bottom?

badboybudah22
10-09-2009, 05:31 AM
Great story, it was written very well.

Shamilah
10-14-2009, 07:07 AM
it's all true hun

RodeoVoid
11-17-2009, 09:07 AM
Wow, that's one scintillating story, Cara. Lucky for you, and lucky for him.

squirtsilly
11-19-2009, 07:17 PM
Hot story, Cara. Quite an adventure and you brought it vividly to life.

I saw that shot of you on your myspace page with the boots. I imagine you've had more than one adventure when wearing those! Very sexy.

Now let me adjust my underwear... :wink:

Shamilah
11-28-2009, 08:24 AM
hmmm,i tend to get more attention in those boots,haha!!