1. Fucking My Sissy Computer Tech


    Date: 10/13/2015, Categories: Anal, Gay Male, Mature, Author: captjim51, Rating: 92, Source: xHamster

    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 ...