Live shemale cam girl fucking boss

THE BEGINNING OF A LIVE SHEMALE CHAT GIRL

I have always looked feminine even when I was  starting hormones. There were plenty of times I would blow guys back in high school. You could say that I was somewhat very popular with bisexual guys. I always enjoyed being a bottom feeling a hard cock deep in my ass was always amazing. And there was never a time I was short of getting a hard cock. So you could call me a floozy or just a male bisexual cock slut. You could find me dressing up in my sisters short skirts or stealing her dildo while she was out with her boyfriend. I was always horny so it was no wonder why cock was always in my mouth. Although the fun really started when I went all out and began hormones in collage. I would always go into the the live shemale cam shows to study their moves and attitudes.

HORNY COLLAGE TRANSSEXUAL

Furthermore I was never to into doing the fucking until I got into collage. When I got a part time job as a secretary at a car lot close to campus. By that time I was very developed into a sexy shemale you could say. At night after work I would do live shemale shows to boost my confidence and boy did I get it. I never thought of making it full time work until I got caught fucking my boss by his wife. That all started by accident kinda, my boss Jim asked me if I wanted to grab a drink with him and another co worker. Anyway I said yes fully knowing that Jim has always wanted to fuck me and i gave him good reason. I would ware short skirts with my cock almost sticking out they were so short.

DRINKS WITH THE BOSS

There was never a question to people I worked with if I was male. I have looked totally female sense a little before collage. Also I never gave up that information and the straight guys fucking me never said a word. So when I went out with Jim my aim was to suck his big cock without him knowing. Boy was I in for a surprise when I would end up ass fucking him that night. After a few drinks that night Tom who is a co worker said his goodbys. And that is when tom asked me if I wanted to go to his house for a drink. He said his wife was out of town for a few days so I didn’t have to worry about her.

THE REVEILLE OF SHEMALE WEBCAM COCK

I was a little nervous but I wanted to suck his cock so bad that I said sure. Also Jim was bit older then I am used to made me excited and nervous. Then he pored us some drinks and asked if I could look at some files on the computer. What came next I was not expecting at all, not in a million years. He pulled up his book marks and proceeded to got to the tranny cam chat site i performed on. I felt faint and flush my face must have been beet red. Then he laughed and said you did not think I new did you, while he proceeded to go to my live tranny chat profile.

CALLED OUT FOR BEING A SHEMALE SEX SHOW HOST

I said how did you know, he said someone called about a loan application I applied for like a year before. The people on the other end asked for Chris my old legal name, now I go by Christian. He said the people on other end told him another online company I worked for. So after hanging up with them he researched the company. And to his surprise it was a company specializing in shemale sex shows. In addition he did research and found me on there. He then confided in me by telling me how much he has always wanted to be with a sexy transsexual.

THE FORPLAY WITH THE BOSS

At that time there was only one thing to do. I leaned in kissing him and rubbing his already bulging cock. Jim also confided in me telling me how he has always had fantasies about being fucked by a big cock tgirl. Telling me that he has played with a strapon with his wife and how he sucked a cock back in collage. Although he has never had a real throbbing cock inside him. So with that being said I new what my role was here. That was my queue to slowly lift my skirt exposing my semi fully erect cock

MY BOSS LOVES SUCKING TRANNY COCK

For not having very much experience he new exactly what to do. As he slowly engulfed the mushroom tip of the head of my dick sliding his head down my shaft. He definitely had the gift of sucking shemale cock that is a fact. After awhile of him working my dick, it took everything for me not to cum. We worked are way to his bed when I pushed him down on the bed and continued to unbutton his pants. Surprised, is a understatement when his cock sprung out showing me a good 11 to 12 inches of man meat.

THE BOSSES COCK IS MORE THEN A MOUTHFUL

Jim was definitely a mouthful, as I could barley engulf his dick fully. One of my favorite techniques sucking cock is cradling those balls with a finger up my partners asshole. I have always been proud at how fast I could make a straight guy cum in my mouth. Not this time though before he was about to shoot his jizz down my throat. He pushed me back and told me to fuck him in the ass.

MY SHEMALE COCK FUCKING THE BOSSES ASS

So me being the good little transsexual girl I am I proceeded to help him get his clothes off, everything but his tie. I was so eager that all I did was take my panties off leaving my high heels on and skirt. As he bent over gripping the head board I grabbed the lube he brought out on the bedside table. It was cherry flavored witch is my favorite for sucking cock, although gets a little sticky. I crept up behind him stroking my cock under my tiny skirt.

I new he had to be tight so I worked the tip in a while then slowly worked my way in his very tight ass. Carefully taking it easy for the fact of me not wanting to scare him away. I grabbed his tie and whispered in his ear ” is this everything you wanted”, he answered with a yes. As his tight asshole was gripping my cock like a vice her was getting more vocal. Yelling out, fuck me just like that baby, make me your dirty tranny slut.

GIVING THE BOSS SOME TRANNY DOMINATION

I was never much into domination but this was way to hot. While I loosened up a bit, I started smacking his ass grabbing his tie, saying you like that slut. All though while he was yelling out yes just like that baby. You would never have guessed Jims never been fucked before besides being so tight. I could barley hold back from cumming inside him. And then to my surprise he yelled out, cum inside me baby.

GIVING THE BOSS A TRANSSEXUAL CREAMPIE

Me being the obedient little cock slut tranny I am he didn’t have to ask twice. It took me like a split second to release a huge load of cum inside him. Giving him a sloppy dripping cum dripping creampie. I grabbed his tie pulling him back, asking if it was everything he expected? He answered that was amazing! Jim and I got up fondling and kissing as I made my way towards his wife’s makeup table.

THE BOSS FILLING UP MY ASS

I proceeded to put my elbow on the table lifting my skirt with other arm with my ass winking right at him. Jim new exactly what to do with his big dick sticking up at full attention. Jim came up behind me and started rimming my more then ready asshole. After awhile of tongue fucking my puckered asshole. Then while bending over looking at him in the mirror he eased his cock inside me. I have had many big cocks but not as thick as his.

THE FINAL CUMSHOTS

It didn’t take me long before I was loosened up and he was grabbing my hips pounding my ass. So naturally I thought it was only far that he fill my ass with a thick creampie load also. In addition to him fucking my ass and stroking my cock at the same time I shot my load again. I yelled out while he was pounding me, fill me with your cum! That was it, I had jizz dripping out my ass down my leg while he kissed my neck.

From that day forward I was Jims favorite secretary also past time. Until we were caught by his wife, that is another story in itself. Maybe I will find time to write about that next. Or I could write about our adventures of swinging with straight couples!

xoxo

Christine

Author: chatx