This is a print version of story Fucking My Sissy Computer Tech by captjim51 from xHamster.com

Fucking My Sissy Computer Tech


I glanced down as Tim my 21 year old computer tech was sucking on my fully erect cock. Tim 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 sissy 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.”


We met on Monday and our flight to Vegas was uneventful. I got a two bedroom suite at the Mirage. For some inexplicable reason I was attracted to Tim, he did look and act like a girl with his thin body and feminine mannerisms. To tell you the truth he 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 a small black bra, and black panties which covered his small cock. He also had on a garter belt and nylons accented by a shoulder length chestnut brown wig. But what really struck me was how gorgeous he looked; his long thin legs, cute face and flat stomach made him look just like a young girl. His sexy expensive lingerie made him look like he came right out of a Victoria Secrets catalog.

Tim laid back in a sensual pose on the bed. I looked down at this boy/beauty and he said “thanks for helping me last week’ now get in bed and fuck me”. I took my clothes off revealing my older 53 year old construction workers body to him. I stood by the edge of the bed, Tim crawled over to my awaiting eight inch cock. Now I have had some fine women suck my cock. Nobody ever sucked my cock like Tim. Tim took me in his mouth and began a gentle rhythmic sucking which got stronger and stronger each time he inhaled my cock. I just stood by the edge of the bed admiring Tim’s slim body, his clothes, makeup and wig made him look so feminine, the only sign that he was a male was his small erect cock sticking out of his black bikini panties. Tim continued to suck my cock until it was so hard that the next step was obvious. This little baby doll was about to get fucked by an older experienced man who knew how to treat a ladies ass.

Tim then stopped sucking and said “the lube and condoms are in the nightstand, use plenty of lube and be gentle with me at first, I need to get used to your big cock inside me”. With that he lay on his side and exposed his fine ass to me. I grabbed Tim’s hips and positioned him on his side with his ass facing slightly upwards so it would be easy for me to fuck him. I put on a rubber and poured plenty of lube on my cock then I squirted some on my fingers and rubbed it into his awaiting ass. Tim moaned as my finger massaged his prostate. Tim said “Ken you can fuck me now” as I lined my cock up with his rectum I inserted into the finest ass I had ever seen. I slid it in about half way and held it there while Tim got used to a man being inside him. He moaned softly as he began to accommodate my thick eight inch cock in his rectum. Then Tim whispered “give me all of it” and I slid my man meat into this baby dolls ass. I looked down and saw one of the most beautiful boy/women I had ever seen with my cock buried in his ass.

Tim whispered “take me like a girl” as he rolled over on his back, raised his leg upwards, and spread them wide so I could see his fuck hole. I applied some more lube to his now open anal orifice. I crawled into bed with him, kissed him passionately and he French kissed me back like the whore he was. I wasn’t gay or anything but god I wanted this sissy. Then he reached down and moved my cock forward so the head was now in his ass crack. I am pretty inexperienced at all this, but Tim has probably been fucked a hundred times and knew just what to do. He reached down, grabbed my shaft and held it still, and then he maneuvered his ass so my cock was lined up with his anal opening. I pushed forward and soon I felt the head of my cock entering his rectum. Tim let out a soft moan as the head passed his tight outer opening and slid further into his young man pussy. He just held still as he got used to me inside him. Finally, he whispered “fuck me, but do it nice and slow, you’re a pretty big man”.

I have had a lot of women in my life so I knew how to give a nice slow fuck. I gently and slowly ran my engorged manhood in and out of his ass. Tim lay under me moaning like a woman. Every time I thrust forward and my cock reentered his ass he squirmed a little. Then I looked down and this beautiful sissy was reaching into his bra and was massaging his nipples. He was writhing underneath me and every small motion of his body stimulated my cock even more. Here I was fucking Tim for the first time and was finding out I really enjoyed gay sex. I liked being the dominant top.

Then Tim’s right hand came out from under his bra and he began furiously stroking his cock. He made a loud grunt. I looked down and there were gobs of white sperm shooting out of his cock. I knew young guys came a lot, but Tim was shooting load after load all over his stomach. I was so turned on I felt my own load surging from my balls. I shoved my cock all the way into Tim's man pussy, it felt incredible!!! My body tensed and I came filling my rubber with my seed. His tight ass continued to grip my highly charged cock as it brought untold pleasure to me. I buried my cock deep in him as I kept cumming. Tim knew I was cumming and let out another loud scream and yelled “keep fucking me, don’t stop”. Like a good stud I just kept fucking him until his body relaxed and he fell back exhausted. I got off of him, went to the bathroom and cleaned off my cock. I came back and Tim was taking off his nylons and hanging up his dress, he jokingly said “got to take care of my clothes so I look good for you tomorrow?
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A really great, sexy story.  You do know how to treat a lady in bed.
1 year ago
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hot
2 years ago
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Lucky Tim!!! ...Envious Susie
3 years ago
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Nice Sissy Story, I heard they are really into older men. All the vids I see are them getting banged by an older guy.
3 years ago
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beautiful sissy story
3 years ago
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Sweet story, hope there will be more? Start of a good string!
3 years ago
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