1. Finding A Sissy At Work - Dinner In Vegas Pt I


    Date: 11/2/2014, Categories: Anal, Gay Male, Mature, Author: captjim51, Rating: 100, Source: xHamster

    (Note: Part I is interesting to the story, but Part II has more Sex) If you have been following this series you know I own a large construction firm in Kansas where I hired a new computer specialist who I took to Vegas on a business trip. Little did I know he was a young 20 year old Sissy who introduced me the “finer” side of life? I fucked my little Sissy last night for the first time and enjoyed it thoroughly. Now tonight, I was going to meet him/her for dinner at the Jasmine’s one of Bellagio’s best restaurant, who knows who would show up? I got a text from Tim asking me if he could buy something special to wear tonight. I asked how much? Tim texted back, “oh it’s about 500.00”. Well a night of lap dances in Vegas could cost that much. I figured if I bought this stuff for Tim I was sure to get laid. I said, sure go ahead, I’ll make sure you get reimbursed for it on your paycheck. He texted back, you get a table at 7:00 I get there at 7:15, I want to surprise you. Well I booked a table at the Jasmine Room for dinner. It was very expensive French restaurant overlooking the Bellagio’s famous water display. I got there at 8:00, got my table and waited for Tim to show up. Well at 8:15 my slender Sissy Tim entered the room and my jaw almost dropped, along with several of the men’s in the room. My 21 year old slim tall 100 pound Tim was wearing a pale blue two piece charmeuse knee length dress, with a shear outer layer skirt. This was enhanced by his petite figure and gorgeous ...
    legs. Tim’s blue hosiery was followed by a pair of blue four inch heels and a dark black wig down to his mid back. He wore an A cup bra which suited his slim figure, no big boobs sticking out, just the delicate hint of two very small breasts under that beautiful dress. Tim’s makeup was impeccable, the blue eye and face make- up complimented his dress perfectly. Several heads turned when he entered the room, and as he walked to my table he did so in that very feminine way that I liked. He sat at our table and asked how he looked? I responded “you’re the best looking women in this restaurant” no doubt about it. Well Tim ordered some fancy French wine and dinner and we mostly talked about his computer training and how he learned that the “clitch” we experienced at the company was due to the manufacturer of the software and not him. I agreed, because after all I wanted to fuck this sissy’s ass tonight, why argue with him. Then my friend Ron a Construction Equipment Salesmen from my home town headed to our table to say Hi. Tim got up to go fix his blue lipstick in the Women’s bathroom. Ron said “you old dog!!! Are you fucking that cute little thing?” I replied “I sure am, and she’s got the best pussy I have had in years”. I didn’t tell him it was a man-pussy I was fucking, but why did he need to know” Ron excused himself when Tim returned to the table. Tim’s lips were now accented by a dark royal blue lipstick. The feminine dress, the wig and make up made me get hard just looking at ...
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