My sister Lisa and I where real close, her being almost two years older than me. I was always dressing up with her to play house when I was young. When we grew older she continued to have me dress in her clothes when we played. I grew out of it when I turned fifteen and started to hang with my friends.
One weekend we were home alone while our parents where out-of-town. Now she had just turned twenty and I was just out of school myself. We had not been together by our selves for some years. My sister talked me into dressing up in some of her more reveling close. I agreed to do it and then she insisted on doing my hair and makeup. We had a good time reminiscing about people we had gone to school with as she worked her magic on me. When she finished and I looked into the mirror I did not even recognize myself. I looked very hot and could have passed any where as a girl.
We made a few drinks and sat around talking like girls do about other girls we knew and yes, guys we knew. Then the door bell rang and I almost spilled my drink as I jumped to my feet ready to make a quick exit. My sister told me to relax and sit back down, no one will know who you are she told me. She went and answer the front door letting in her old girl friend Sheila who she always hung around with. She had heard that Lisa was back in town for the weekend and stopped by to say hello. Sheila came in and seen me right away saying, she did not know my sister had company. Lisa introduced me as Beth, one of her room mates from college. We sat and chatted with me not saying much but agreeing with what ever they where talking about.
Sheila then invited both of us to a party saying some of their old class mates would be their. I tried to tell them no that I was tired and wanted to stay home and turn in early. I was hoping this was going to get me out of it. Lisa however said it was early and this way I “Beth” could meet some of her friends. Lisa took me to the bathroom to freshen up my lipstick and to put some perfume on me. I protested that she had suggested I go along but she reassured me no one would even know I was Ben. We claimed into Sheila and she drove us to the party in the next town. I was very nervous since I had never went out in drag before. Knowing that I did look good gave me some confidence that I would not be found out.
When we walked in the house had a lot of people partying so that made me a little more relaxed. We managed to get a drink and tried to walk through the crowd and find a place to stand and talk. I recognized several people from our school and some from my class. We stood to one side of the room and as we where talking, Ted one of my buddies came over and asked Lisa if I “Ben” was some where at the party . Lisa told him that I had left early in the day and she did not know where I was. Ted looked at me and I could feel my face turn red and getting light-headed like I was going to pass out thinking he had recognized me. Ted asked Lisa who her lovely friend was? She introduced me as Beth and he asked me if I needed another drink. I told him no so he told us he was going to mingle with others but would be back. I was relieved he did not recognize me dressed like a girl but also boosted my confidence.
I decided to walk through the crowd and check out who all was there. I seen a couple of girls and another guy that I graduated with but none seemed to recognize me as I continued through the crowd. I decided to go find the bathroom which I found to have a line of girls waiting for there turn so I decided maybe I could find a place outside to re-leave my bladder. When I walked outside Ted was standing their which made me stop dead in my foot steps. Just then he saw me and called my girl name Beth, asking if I was leaving? I told him now I just needed some fresh air as he came over to talk. We talked about nothing really as he said let’s go get a drink which took my mind off having to go pee. He seemed to take a real interest in me and I wanted to get away from him before he found out who I was. I told him I needed the bathroom so I left him and stood in line.
Latter that evening since no one recognized me, I was quite confident not to be found out. I was feeling my drinks now and felt more daring throwing caution to the side. Ted found me once again so I led him on which he was enjoying. He told me that I was hot so I figured he was feeling no pain either. Then out of no where he kissed me on the mouth. This caught me off guard but without thinking I kissed him back. Then I realized what was happening so I pushed him away. Ted asked if the kiss pissed me off? I told him no as he was apologizing. Then it realized I had become aroused from it which I could not figure out why. So many thoughts rushing through my head as he grabbed me by the waist planting another kiss on my lips. I do not know if it was the booze or what but this time I just went along with it. Kissing him back as he squeezed my ass I felt like girl who wanted more. Before I realized what was happening he had led me to bedroom closing the door behind us and locked it.
I was so out of it that I tried to resist but could not fight him off being so intoxicated. He held me down on the bed and started to rape me. I could not do anything to stop him. When He found out that I had a stuffed bra I remember him saying, what the hell you don’t have any tits. Then when he pulled down my panties seeing my cock he jumped back saying you a fucking dude, what the hell is going on here? I slurred out words of apologizing for being dressed like a girl as he told me he was going to have me suck his cock. Trying to fight him off with not much luck he stuck his hard cock down my throat pumping in and out until he climaxed.
Once done he noticed my erection asking if I liked it? I told him now but my cock was saying different and he pointed that out to me. Then he laid down beside me, masturbating my cock until I spurt cum. Then he french kissed me on the mouth as I returned the favor. He helped me get dressed and once we returned to the party most everyone was gone including my sister and Sheila. Asking me where I lived he was going to take me home. I could not remember my address being so drunk she took me to his place. He striped off all my clothes and put me in his bed as he joined me. I barely remember him feeling my cock as I passed out. Waking up the next day I was shocked to find myself in his bed wondering what happened to me. Ted woke and said, Ben you’r a hot chick when you dress as Beth. Knowing he knew, I remembered what led up to me being in his bed. I dressed in my girly cloths as he watched making me feel as if I had to throw up.
Ted asked if I would hang around for a while before leaving? He told me my secret was safe with him. I said to him I had to get home and apologized for being dressed like I was. He was happy to see me again and told me he preferred me as Beth. He took me home and I went straight to the bathroom to take a shower. When I came out Lisa came out of her room and asked how my night was? I asked her why her and Sheila left me at the party? Lisa said that Ted knew who you where Ben and said he would see to it that you made it home safely. Ted knew who I was? Yes she said. I went to my room to sleep some more wondering how long he knew.
That evening Ted called and asked if it was alright to come by and pickup Beth for a date. I told him no and that I really did not want to see him again. Lisa had been listening to our conversation so when I hung up she asked why I did not want to go out with Ted. She told me that he had said to her that her really was turned on by Beth and he said she was hot. I felt my cock swell to the words she said. I started to cry and say it was all a big mistake. Lisa told me that it was all okay and she knew Ted had sex with me. I asked her how she knew? He told me before he took you to the bedroom and I told him I figured you would go along with it. Ted cares about you and I think deep inside you like being Beth, am I right she asked? Looking up at her I said yes I did enjoy being Beth but did not want to date Ted. Lisa asked who I wanted to date? I said no one I just liked dressing as Beth, then she told me she would help me dress up again. Taking my hand she led me to the bathroom to start my makeover.
While Lisa worked her magic on me, turning Ben into hot looking Beth. She talked about Ted and how interested he was in Beth. She said that he would make a nice boyfriend for me and that since he was a friend of mine, we knew each others likes and dislikes. Before she had finished my hair and makeup she had me convinced to go out with Ted that evening. I have since moved in with Ted and dress as Beth all the time now. I have taken makeup lessons and researched things on the internet. Ted paid for my hormone treatments so I now have small breasts. I have been living as Beth for five years now with Ted. He has been talking about marring me and we have started on the weeding plans.
“SM” Sissy Maker