1. Finding A Sissy At Work -Dinner in Vegas Part II


    Date: 3/24/2016, Categories: Anal, Gay Male, Shemales, Author: captjim51, Rating: 100, Source: xHamster

    A few minutes later, I heard Tim call from the bedroom “Ken I’m ready, come on in” I thought God am I lucky, I’m really going to fuck this little doll all night. 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 dark blue boustierre, blue see through panties that were holding his small dick in place, and a blue garter belt and sheer light blue nylons. His dark hair flowed down the left side of his face. He still had his four inch stiletto heels on. But what really struck me was how gorgeous he looked; his long black wig surrounded his beautiful face. His makeup made him look like a Victoria Secrets model. I was already in my robe which dropped to the floor. I stood at the edge of the bed. Now one thing young Tim knew how to do was suck cock. He started by running his tongue up and down my shaft, then his lips took over as he gently sucked the head into his mouth. Then he began kissing the shaft until it was as hard as it was going to get. Then he did his “specialty” he just put the head of my cock in my mouth and then all of a sudden I lowered his head taking the entire cock in his mouth down to the base. Tim kept “deep throating” me like this for several minutes alternating by sucking by licking my cock and then roaming gently to my balls sucking them into his mouth. I moaned “suck it baby, suck it good”. Then I knew from my years of experience that I was about to shoot my ...
    first load, “I said I’m cumming!!! And Tim took the entire cock in his mouth as I shot several loads down his throat. I knew from the night before that Tim was a “swallower” and sure enough he drank every drop of cum out of me. Tim then slowly licked and kissed my dick to clean me up, as my hard on subsided. We both lay back on the bed breathing heavily, after a few minutes rest, I asked “how do you want me to fuck you? Tim replied, doggie me at first then I’ll ride your cock until you cum again. I put Tim on all fours on the bed I moved his body so my cock was lined up with his awaiting throbbing rosebud. The I inserted one finger inside him as I spread lube all over my rubber and his ass. Then I inserted a second and then a third finger, rotating them to open Tim’s anal orifice. Soon he began moaning softly and rocking his hips back and forth to meet the three fingers that were massaging his ass. Then Tim said “I’m ready”. I got in bed and mounted Tim and placed my cock head against his anal opening. Now I knew Tim had been taking it up the ass for years, so he hardly felt my cock entering his ass. I grabbed his hips giving him about half of my cock, but I knew from Tim’s grunts that it felt good as I slowly moved my cock in and out of his ass. Tim knew I was teasing him by giving him only half my cock. Tim said “here I am the most beautiful Sissy in Vegas and you are teasing me!!! He then said "Don don't tease me, I want that whole cock right now!!!” so I immediately thrust ...
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