This is another true story about one of the times when I was all dressed up as Josie. Sorry kinda long, but figured it would make the story better.
I was in the middle of moving to another city and had to stay with my parents for a couple of weeks until my new apartment was ready. I would stay with my parents for holidays and random occasions while in college and had not stayed there for that long since I was in high school. My old bedroom was turned into their new office and the only bed available was my sister’s who is two years younger than me. I spent many days in high school dressing up in her clothes, however had a decent collection of my own that happened to be with me since I was moving.
At that time i had a gf, but we were always off and on and my decision to move to a city six hours away did not help the matter. We were planning on seeing how things go once I got settled in. I recently started meeting people while dressed up,especially during my off times with my gf. She was one that got me back into dressing up since not dressing up in college until this point.
I was bored at my parents house after the first couple of days catching up with them and my friends back home. There was someone that I would occasionally email back on forth with while I lived in my old city that lived in my hometown. They grew up in the same neighborhood and was older, around 40ish. I would email him from time to time, during the times I would dress up and I was in the mood. Just kinda flirted and talked about fantasies. I thought why not and emailed him, at first not telling him I was home.
One night I had the house to myself, my parents went out with friends or something. I thought that would be a perfect night to dress up like old times. I got all dolled up and even put on one of my sisters dresses from her closet, a sexy red mini dress that matched my black pumps perfectly. I was looking really good and was feeling super girlie and decided to email the guy again, letting him know I was in town. I sent a pic of me dressed up without my face because I would still so nervous and was surprised I went this far. He immediately responded asking me where I was staying and pleading with me to come meet him. At this point I was having second thoughts, but the idea meeting him was getting to hard to resist.
We started emailing back and forth, and he has the sense I was being hesitant. He said we could meet by a shopping complex on the side street that is very secluded and empty at this time of night,around 10PM. My hometown is in a suburb and dies down pretty early at night. I knew the place he was talking about and agreed in a moment of feeling extra fem. I put on a sweatshirt and sweatpants over my girlie clothes, took off my wig and heels and placed them in a bag. I brought some lip stick to touch up and decided to drive with my make up still on with my hood up trying to hid my face as best I could. I figured it was dark and I would pass many people if at all if I took side streets.
I hopped into my car with my bag, still so nervous, but excited and girlie at the same time. It took me about 7 min to get to the street and park my car. I looked around me and there wasn’t any cars by me and no one outside that I could see. I decided why not and took off my sweatpants and sweatshirt, and threw my wig on as quickly as possible. I put my heels on and touched up my lips and sat in the car, frozen with fear and my heart beating super intensely. I looked around and still nothing. I picked up my phone to see if he emailed me and had no response so I told him that I was there and parked in my car. I waited for ten min and no response so I drove off and went back home, confused but high from the experience none the less.
I went to sleep and woke up the next day to an email asking where I was. He said he left his phone at his house in a rush and waited on the street. We found out I was at a different location! It happened to be a weekday and my parents were both working and so I showered and got ready to dress up again. I picked another of my sisters dresses a long sleeved pink mini dress that was from forever 21 or a store like that. I wore my 5 in bright blue heels and did my makeup using some of my sisters stuff in her room. I emailed him back and asked what he was doing.
He responded that he was at work but in our neighborhood on the job. He worked for the city or something in a truck fixing things on the Road or something to that extent. He asked where I was specifically and I told him the cross streets. He emailed back and said he knew exactly where that was and could be over in 10 min. I was again super nervous, especially because it was during the day something I have never done previously, and because it would be at my parents house. After sitting there for a couple of mins, I emailed him the address and agreed. He responded by saying, “be there in 10.” I immediately regretted it but knew it was too late, so I touched up my make up instead. After ten mins I look out the door and see a work truck pull up and knew it was him.
I opened the door real quick and motioned to come this way. He walked out of his truck, he was about 6’2 240, with muscles and a little chunky. He looked exactly like a construction worker or road servicemen and could not stop staring at me. He told me how good I looked and said he did not think I looked the way I did. I took him into my sister’s bedroom and sat him on the bed. I was super nervous and didn’t know what to do. He slid up next to me and put his hand on my thigh. I melted and knew what I was about to do. He looked at me and started brushing my wig with his fingers and told me to get down on my knees. He took off his belt and started taking off his work pants. His dick was rock hard and pointed out of his boxers. I took them off and took his dick into my hands and started to go up and down. I felt so dirty and so fem and so natural in this state.
I couldn’t resist and moved my lips to his cock and took him all in my mouth. This was only my third time sucking a dick and I felt emotions of excitement and shame. He starts moaning louder and louder telling me what I good girl I was. This turned me on even more and I began sucking dick like a porn star hehe. He told me he was going to cum soon and told me to stick my tongue out. I did what I was told and after five seconds he finished all over me. He got up and left in a hurry, leaving me on the floor of my sister’s room. The thoughts of ultimate femininity and shame popped up into my head. I quickly snapped out because I knew i had to wash my sister’s dress so she would never find out.
Source: reddit.com/r/gonewildstories/comments/lkwd3j/being_naughty_in_my_sisters_bedroom