"Stories 18+" Sam's Sissy Computer Tech

Stories 18+ Sam's Sissy Computer Tech
Since my first day at work as a computer specialist at C@T Construction I desperately wanted to have sex with Sam the owner. He was a stronger older man, divorced and in his early fifties. He started his company with a bulldozer and a dump truck and now it had 300 employees and over 100 pieces of equipment. Every day I worked around these beefy men and went home and masturbated furiously. Here I was a 110 pound, sissy, effeminate, gay twink surrounded by these manly specimens. I was dying to be fucked by one of them, hopefully Sam and hoped to be his “girl” one day. I just had to find the opportunity.

Well C@T bought a new computer system and it was my job to keep it going. I soon became indispensable and Sam knew it. I saved him millions of dollars a year. Well, one Saturday a friend and I went clubbing and I put on some very sexy gay boyish clothing and a small amount of make-up, but I wasn’t all dressed up. We were walking to my car when we met Sam and I was somewhat embarrassed, so I just said Hi. 

The next week at work Sam unexpectedly came up to me and said; “the manufacturer is adding something to the computer system, I want you in Vegas next week for the seminar”. And by the way, I’ll be there for the Asphalt Paving Show will stay at the Bellagio. I could have passed out right then and there. Here was an opportunity to make a play for Sam; my wildest dreams were coming true. I would find out if Sam was gay and I would be the lucky recipient of that piece of information. 

I couldn’t decide what to pack for the trip. I chose my tightest most feminine male clothes, and several of my favorite sissy outfits. I brought my usual, make-up, wigs, Victoria Secrets bra’s panties, corsets, nylons and garter belts. But I also brought my most expensive Royal Blue cocktail dress and a black short “fuck me” dress. In full make-up I would look stunning, like I always do. 

The plane trip to Vegas and the seminar were boring. Sam asked me to dinner and he mostly talked about the company. But I had my gay radar on and sensed he wanted to get to know me better and not in the usual way. I decided to really come on to Sam. I made a very risky bold move when I took his hand once and put my arm on his shoulder. On the way to our room I brushed up against him several times. He said nothing, which meant he was OK with me flirting with him. Sam would have to be blind, deaf and dumb to not know I was coming on to him. I just couldn’t hold back much longer even if it meant my job, I had to let him fuck me, and fuck me right now!!! 

We got back to our two bedroom suite sat on the sofa and poured some drinks. Then I asked Sam “have you ever seen a female impersonator”? He replied yes, so I told him I was an impersonator and would love to put on a short show for him tonight. Sam said, well it’s early, why not. I whispered in his ear “I really make a very fine girl, but it will take a few minutes to get ready”. That’s all I needed to hear. I headed to my bedroom got my long shoulder length brunette wig and put on my make-up. I decided to wear the drop dead sexy royal blue cocktail dress, blue nylons, blue bra and panties and a blue garter belt and blue six inch heels. With my thin figure, girlish face and feminine mannerisms I was one of the best looking cross-dressers in Vegas and that’s saying a lot. 

I came out and you could see Sam’s jaw drop open. He said “you’re better looking than any women I’ve seen today”. I did a dance for him which ended with me taking off my dress. As I stood there in my sexy lingerie I said to Sam, I’m gay, and I’ve wanted you since I met you”. I even put your picture in my living room and admired you every time I looked at it. I said Sam “ you can have me if you want to”. 

Sam answered by shedding his clothes and heading to my bedroom. I looked at him and admired his older yet very strong muscular body. I was one lucky girl tonight!!! I looked at the organ I would have to take inside me. His cock was only about six inches long but it had a very wide girth. I didn’t know if I could fit something that wide in my small girly mouth. As for my ass enough men had plowed that hole I could have taken a baseball bat up that ass. 

Tonight, I had taken the risk of dressing up for Sam and it had paid off. I softly whispered in his ear “do you want to fuck me”? Sam said, “of course I want to fuck you, I’m bisexual”, so let’s lay back on the bed so we can enjoy our first time together. I was so happy; tears began to stream down my face. Sam lay back on the bed, my head went down between Sam’s legs and I proceeded to lovingly kiss Sam’s flaccid cock. I loved the feel of a man’s cock in my mouth, the round tubular organ going in and out of my mouth was a sissy’s dream. The sensations from a warm wet penis inside me stimulated my feminine urges. I knew Sam must be looking at my long hair as my head went up and down while I sucked his manly cock. Soon he was totally rigid and I began sucking him as only a gay man could. I sucked just the head of his cock, and then I ran my tongue up and down his shaft. Then I licked the helmet area where the head of the cock meets the shaft. I knew he liked it when I gulped down almost all of his cock in my mouth holding it there while he experienced me pleasuring him.

I always liked spending a lot of time on my lover’s cock. After all, it is a man’s most sensitive sex organ and Sam’s cock deserved my full attention. My specialty was to take a cock from two directions. My mouth took the top two inches of Sam’s cock and my hand smoothly stroked the bottom three inches. Now and then I would just swallow the whole cock all the way down my mouth. With Sam’s big round cock I had to open my mouth as wide as possible so I could accommodate its girth. I couldn’t deep throat him well, so I tried a new and exciting technique that I used on my other lover’s and I knew he would like it also. I began to gently suck his balls and then slowly licked Sam’s shaft until I reach to tip of his cock. Then I inserted the tip of my tongue down his pee slit at the head of his dick. Then I ran my tongue in and out of the slit. I paused to suck his balls and then returned again to lick his pee slit. No man can take this treatment for very long. Sure enough, I tasted Sam’s pre-cum and soon his whole organ was shooting his cum right in my mouth. I’m a “swallower” I just love the taste of a man’s cum in my mouth. This time it was no exception as I gulped down Sam’s sperm. Sam was moaning in ecstasy as I gave him the best head he had been given in a long time. He fell back and I went and got my drink to wash his cum down my throat. Then I lay back waiting for him to rest so he could take my young ass. 

PostScript: It’s been six months since Sam first fucked me in Vegas. Now he pays the rent on my luxury apartment, pays for my “special” wardrobe, the lease on my new Ford Mustang and my salary has doubled!!!