My First Time as a Sissy

I had moved away from home to go to college at 18. I had been cross dressing secretly for a few years. I would sneak into my mom's closet and "borrow," her clothes. I had my own apartment my parents were helping to pay for. I also had a part time job and was able to buy a few feminine clothes for me to wear. I loved the feeling of wearing women's clothes but, was not very experienced sexually. I had one girlfriend in high school and she was the limit of my sexual experience.

One Friday afternoon I had got out of class early. I decided to spend it dressed in my apartment, watching transvestite porn I had got from the local video store, smoking a little dope and dressing up. I had a black mini dress, black thigh high stockings, a black thong and black bra on. I was wearing a gold bracelet, neck chain and my only pair of feminine earrings. My brown hair was fairly long and I had put on makeup as best as I knew how at the time. I was setting back dressed, getting a little stoned and watching porn when someone knocked at my door.

I had left a request for the garbage disposal to be fixed earlier in the week but, didn't figure they would be out on Friday afternoon. I tried to ignore the door but, the maintenance guy must have heard the tv and used his master key to get in. He entered and saw me dressed.

He said," what have we here? I thought a guy lived in this apartment."

It dawned on him that I was the guy. He said that it was his lucky day finding a pretty girl waiting for him on his last stop. He introduced himself as Raoul. He was a nice looking guy, Hispanic, in good shape and about 5' 10".

He noticed what I had on tv and said he could stay a while. I said that I didn't know him. He said that I would get to know him if I wanted him to keep my little secret. I saw I didn't have much choice. He asked if I could get him a drink. I didn't have much alcoholic but, offered him a wine cooler. I gave it to him and started to sit down across from him but, he patted the couch next to him and he said sit right here. I didn't have much choice so I did. He put his arm around me and said play the movie you were watching.

He started to pull me in close to kiss me. I resisted at first but, found I enjoyed feeling like a girl and getting kissed. I started kissing back. My emotions were totally confused. I was enjoying being kissed but, guilty for feeling like I might be gay. He sensed this and told me to relax that he wouldn't hurt me. I did and felt strangely protected. On the screen there was a shemale giving a guy a blowjob. He pointed at it and said that I should try it. I said that I wasn't into that. He said that if I tried it I would be and that all sissies loved sucking cock.. I was definitely turned on from the kissing and the petting and was very curious about his cock.

He pushed me down on my knees in front of him. I rubbed his cock through his jeans which he liked. He told me to unbuckle his pants and I did. He leaned up and slid them down. There I was on my knees inches from my first cock. It was beautiful, cut and maybe five or six inches long, definitely bigger than mine.

He said,"yeah suck it baby."

I reached out and touched it with my hand and started rubbing it a little. He said that was nice but he wanted my mouth. I was nervous but, excited at the same time. I reached out and kissed my first cock. I had gotten a couple of blowjobs from my girlfriend in high school and heaven knows I had watched a lot of porn so I had an idea of what to do. I swirled my tongue around the head and he groaned. I then started licking up and down the shaft and he was really getting into it. I sucked on his balls and he groaned again then put his hand on my head and guided his cock in my mouth. I was really getting into it too. I had never been so turned on in my life. He started face fucking me and calling me his little sissy cocksucker. I was enjoying this more than I could have imagined. He told me he was about to cum and that I had better take it all. He erupted and I tried to swallow it all but, some leaked out of my mouth. I licked it off like I had seen porn starts do in movies. He leaned back and said that I was a good cocksucker.

He stood up after a few minute and said that he had to go but, he would be back any time he wanted and I would take care of him or my little secret would be out. He then asked me if I enjoyed it. I hesitated at first but, admitted I had loved it and would suck his cock any time he wanted. He kissed my cheek and said he might do more than that in the future.