After my wife found about my crossdressing, she left me and I lived all by myself. I also came out to my friends and most of them were supportive. When I am at home, I would always get dressed and spent my time as a woman. I went out in public occasionally, sometimes with my other crossdresser friends. I was living as a woman mostly, except at work.
One time, my straight friend who just came out of a divorce need a place to stay. He was struggling to make a living and needed help. He asked me if he could stay at my house for a few months till he was able to afford rent. He had helped me in the past and I wanted him to do better so I said yes. But I did mention to him that I would be dressed most of the times and he might find it awkward. He said he was okay with it and a couple days later he moved in.
At first, it was a little odd having to share the house with him as I was a little nervous about getting dressed up in front of him. One night after work, I got dressed up and showed him how I looked. He looked surprised even though he had seen my photos as a woman.
He complimented how gorgeous I looked and slowly I started to feel comfortable being dressed around him. I started to dress more frequently in front of him and he also got used to seeing me as a woman. He was cool about it and most of the times complimented me by saying I look beautiful than most women out there.
Everything was going good and he was able to get a job at a delivery company. Most nights, I would cook and we would have dinner together. One night, he jokingly said that sometimes he feels like he has a wife since I was cooking most of the time. I took it as a compliment and I was also starting to enjoy his company. Its been quite some time that I was living alone and a having a company was nice around the house.
One night, we were having dinner and my friend had brought a nice wine to thank me for helping him. We opened the bottle, started drinking and we were having a fun conversation. We were both starting to get a little tipsy and after dinner I was doing the dishes.
Suddenly, my friend came up behind me and put his hands on my hips, hugged me and kissed my cheeks. I was really surprised and asked him what he was doing. He apologized and said he didn’t know, he just had a sudden urge to be close. I told him maybe he had enough to drink and go watch TV. He nodded and left.
When I was done with the dishes, I went to the living room and sat on the sofa next to him. We were watching a talk show on the TV when he said I was looking really beautiful that night. I blushed a little and suddenly he leaned over and kissed me on my lips. I pushed him back and asked him what’s going on because I knew he was straight. He replied that when I’m wearing a dress and makeup he sees a woman and forgets I’m a man.
He confessed he was getting attracted to me for some times now and didn’t know how to tell me. He told me he missed his wife sometimes and seeing me in my feminine mode, he really feels like I am a very beautiful woman. I said I didn’t know he felt like that, although honestly I was flattered. We were both silent for a while and he asked me whether I was attracted to guys or been with any guy before. I replied not yet but sometimes I did wonder about being with a guy and making love.
I could sense that he was making a move on me and I didn’t know how to react. He was my friend after all and it was a little weird. So, I got up and told him I was going to bed. He looked a bit down and told me to stay with him for a while. I said I was tired and started walking away.
He then grabbed my hand and pulled me back on his lap. We were face to face and he kissed me. I was a little shocked but somehow I didn’t resist. Then he started to move his hands over my body and squeezed my butt while we were kissing. I could feel his thing getting pretty hard below me. I was somehow satisfied that I was getting him turned on. I was nervous but the sensation was very intense that I couldn’t resist. I was getting turned on too.
We were kissing each other pretty intensely and then he started kissing on my neck. I slid my hands and started to stroke his thing. I was surprised by the size of it, it was pretty big. Then felt like he couldn’t wait any longer so he stood me up, turned me around and unzipped my dress. Then he was unclipping my bra but I told him to leave them on. Then he removed all of his clothes and pushed me back on the couch.
He got me on my back, took off my panties and he was inside me. I wasn’t expecting it to be that quick but it was. I had some experience with toys before but this was pretty extreme. I have to admit it was painful so I had to tell him to stop.
I got up and went to my room to get some lube and he followed. I found the lube and he was really anxious to apply it and get back to business. We had a very intense moment together and finally he came inside me. It was something I had never experienced before and I was pretty exhausted after that. After that I slipped into a nightie and we both cuddled together and I don’t remember when I dozed off.
The next morning, I woke up and found myself still wearing my nightie with my makeup and hair wig on. Of course, I looked super messy and also felt quite sore in my bottom but it was a beautiful experience that I had the night before. It took some time for me to analyze what really happened last night.
My friend was already up and I found him in the kitchen cooking breakfast. He smiled when I entered and said I was great in bed last night. I replied he was great too. He asked me if things would get weird between us now and I said no. He smiled and said he felt really good after last night. We chatted over breakfast and he was off to work because his shift started early. I felt like I was his wife and it was a beautiful feeling.
After that moment, we did share couple of similar moments but we both agreed that it wasn’t really right to get into a relationship together. After 1 month, he moved out and what we shared together was a secret just between us.
Story submitted by Sophia.