My name is Alyssa, Aly for short. This is my story of how my life took a complete 180 degree turn, a turn i never expected. My sister in law and her fiancé had just moved into their new place and my wife and I came over to help them move. My sister in law was very attractive and I always was in awe of how she looked and dressed. Her fiance was a nice and attractive guy that any girl would be lucky to have. We all got shit faced drunk and my wife and her sister went and passed out in the bed. Her fiancé, Max, and I were still drinking when I blurted out I like to crossdress. He said "wtf" and asked if I was passable. I told him I thought so. He got a box of his fiance's clothes and said "try something on, you're close to her size". I went into the bathroom and shaved my legs arms and chest. I found her makeup and started doing my makeup. Well I put on a blue dress, stuffed the bra, and got into her 5 in sparkly heels. I said the only thing I was missing was a wig and he opened the bathroom door and tossed me a blonde wig, saying he found it in their Halloween supplies. I put it on and straighten my hair. I was extremely nervous but had the privilege of liquid courage. It was the first time I would show anyone I knew that I dressed as a woman and that was terrifying. I took a breath and I went out and he saw me and said "holy shit".
We continued to drink and then he asked me to sit next to him. I did and he put his arm around me. and I was kinda shocked. Here I was a married man, dressed in my sister in laws clothes and her fiance had put his arms around me. I was kinda getting turned on. I then looked up and we started kissing. I felt up his chest and then down to his dick. It was hard so I undid his pants and was giving him a handjob. I then said "enjoy this" as I went down on him. I started bobbing up and down on his cock and then I tasted the precum and went crazy. His cock was very straight and hard. All I wanted at that moment was to please him and make sure I was better than his fiance at everything. I wanted him to think only of me as I was moving up and down on his cock. I could taste the precum still as I was looking into his eyes. I went faster and then he held my head down as he started to cum. I swallowed it then went to the bathroom. I could taste the the cum and it was somewhat salty but I loved the taste. I wanted more of him inside me. I came back out and he still had his pants off and he was hard again. He grabbed me and forced me on the couch were he pulled down my panties and shoved his cock in my ass. I screamed in pain but as it loosened up I started moving with it and moaning. It was tense at first and very painful. As i loosened up, all I could feel was the pleasure. It was like heaven. I started mouthing the words "oh yes" to him as he thrust in and out. I started to push my ass into it to and moving with his thrust. I then wrapped my legs around him and we were kissing. He started going harder and faster till he came deep in my ass. We continued kissing and he whispered I was the hottest girl he's ever fucked. I kissed him again and we spent the next few hours kissing and Cuddling.
We had talked maybe once or twice in the days following. We didn't really mention the sex but he did comment on how he missed my legs around him. He was honestly all I thought about for days. I wanted to be his girl, every time I saw my sister in law I wished I was in her place, being in bed with him and being kissed by him. Like 3 days later we were having a BBQ before my wife went to work and before his fiancé was going on a business trip. His fiancé was in this yellow floral print sundress and had 5 in white wedges on with her hair in a pony tail. I got a text from him saying "you're wearing that tonight" I responded with a smiley face. That night after my wife left I went over but I had already dressed up in a tank, sweater, skirt and sandals with my makeup done and he kissed me at the door. He told me the clothes were in their room I went in and changed into the dress and wedges and put my hair up like hers was. I came out and he said... Omg U can be her fucking twin. I giggled, I enjoyed the fact that he thought of me as her equal and that I was the one he wanted. As I pulled him in and we were making out.Our lips were meeting and we moved to the couch. Where he pulled me onto his lap and we continued kissing. I felt him getting hard and I moved to his side and pulled off his pants. I stroked him hard and I pulled his underwear off and slid his dick into my mouth.I began kissing his dick and then took it all in my mouth. I was at a quick pace when I began to fondle his balls with my hands. I started to taste his precum and I loved it. When he was about to cum he pulled out and came all over my face. I went to the bathroom and cleaned up and redid my makeup as I was fixing my hair he came in and was holding me from behind and I felt him go straight in me. We were kissing and he was fucking me from behind till he through me on the bed. We got into missionary and he was kissing all over my neck as he was thrusting and I was moaning. It felt so good having him deep inside me and thrusting hard. I said yes so much more. He picked up the pace and I pulled him in tight as I met his lips with mine. When I arched my back he grabbed me by my hair and pulled down fucking so hard just then I started cumming and screaming for more and he kissed my lips and starting frenching me. He picked up the pace and I moaned and kissed till I felt him tense up and just start Cumming in my ass. We kissed and talked. At the end of the night he asked me to run away with him and he would make me his "wife". I was scared, it was a chance to get over my jealousy of his fiance and be her replacement. To be in her shoes daily and know I had someone like him. But it meant leaving the comfortable life I had built for myself. I got excited thinking about it and knew that I had to move away. It took some time on my decision but 2 weeks later I text him yes take me away. Him and I moved about 4 hours away and he helped pay for several surgical procedures to make me more feminine. Now today, I live as his loving wife.