Finding a Sissy At Work Part 1 - Sex Stories

Finding a Sissy At Work Part 1

I glanced down and Tim was sucking on my fully erect cock, he was dressed in a black bra, black lace panties, and a garter belt and nylons. His long dark hair was accented by his flawless make up. Tim looked like the nineteen year old petite little nylon clad baby doll that he was. I looked down as his head bobbed up and down my growing cock. I wondered “how the hell did this happen”. I own a large construction firm in Kansas and knew I had to hire someone to run our new computer system. I left this to my secretary and when I came to work on Monday there was a thin boyish looking guy in the new computer room. I asked my secretary Kate “is that a girl or a guy”? She laughed and said “he’s a guy; his name is Tim, although with some women’s clothes and makeup he would make a gorgeous little thing” A few weeks went by and one day I heard someone crying in the office, I got up and found Kate consoling Tim who was crying on her shoulder. I asked “what’s wrong” and Kate said “Tim just lost two weeks of data entries he had made into the new system; he worked every day until eight at night and even worked on it on Saturdays”. Tim sat in his chair with his hands in his face sobbing saying “all my work, all my work is gone; you are going to fire me”. Well it’s my job as owner of this company to solve problems. I had a friend who was a computer instructor at the local college. I called him up and in four hours he had recovered all the work. He suggested I have Tim take a week long ...

... seminar to learn more about some “glitches” that the manufacturer had in the system. I called Tim in the next day and told him “here are our plane tickets we are both going to Vegas to figure this thing out, plus the heavy equipment manufactures exposition is the same week so I can kill two birds with one stone. We’ll get a suite at the Mirage; see you at the airport on Monday.” I met Tim at the gate and just by watching him walk down the concourse you could see he exuded sensuality. His 5’ 1” thin body was accented by a pair of long legs and an ass that screamed “f*ck me”. I thought “this is great, everyone will think I am this guy’s sugar daddy taking him to Vegas for who knows what”. We sat on the plane and Tim’s feminine mannerisms became more evident. To tell you the truth it kind of turned me on. I told Tim I would meet him back at the room and we would go to dinner and play the slots, I said “don’t worry about the money, I’ll give you $500.00 if you win, I get half the winnings”. Well, the night we met back at the suite and went out for dinner, Tim made a good hit on the slots and won $1,200. We went back to our two bedroom suite and I showered and got ready for bed. Tim seemed to be spending a long time in the bathroom and I would soon find out why. I heard Tim call from his bedroom “Ken I’m ready, come on in” I thought what? Well, I went into Tim’s room and there he was lying across the bed. He looked like a living doll; he could have been a fashion model. Tim was wearing ...