Making Love To A Crossdresser

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Making Love To A Crossdresser
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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.
That was so nice of a story. It is a dream that we ( Trans-women ) would surely like to come true. Even to the point of a marriage. I love it.
Lovely story. I wanted them to stay together, though! Maybe you could reunite them in a sequel – maybe they’ll even get married 😚
What a lovely story… I dream with something like that… I really would love to feel as I am the wife of a guy, sharing things at home, and having a romantic encounter…
If I could be that guy it would be a thrill for me too.
Before starting my transition I was a CD. I enjoyed being a woman not realizing I was suffering from gender dysphoria. Never once did I even think I’d be with a man. I’m a trans lesbian so after reading about this encounter it has me wondering. I’m hoping they are still friends.
Hot story! Sounds like a wonderful experience.
What a lovely and romantic story. I’m glad you remained friends and even lovers, at least for a while. There is always an awkwardness after two friends move to a sexual relationship.
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My First Time Cross Dressing WITH PICTURES

In 2015 I came out as transgender & started my transition from male to female. My purpose here is to share my triumphs & my struggles in hope to help others find a true sense of self. So be prepared for new content on: fashion, makeup, LGBT & life. Don’t be afraid to interact with me on social media and make sure you guys subscribe to my newsletter.
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It was freshman year of high school and I was friends with a few girls and for Halloween, we all wanted to get together and do this little trick-or-treat night together. I had never gone out trick-or-treating on my own. They were all like, “oh my God you should dress up like a girl, you should fully dress up like a girl” and “yes do it. Do it! DO IT!” and I’m like “fine, I’ll do it.” 
In preparation for that night, I asked one of my friends to do my makeup. She brought her makeup to school and we literally sat on the bench during lunch and she did my makeup in the middle of the Courtyard at my high school. Then I just loaded up a bag full of the clothes I was going to wear that night and the wig and whatnot. I got like a $12 wig and this outfit though, you guys, kills me! I had some gloves from Hot Topic and my dress is actually a skirt from White House Black Market, I had borrowed it from my aunt. I was also wearing some women’s shoes too. I don’t think I have pictures of them, but they were also from my aunt. I borrowed the majority of my outfit from my aunt with a necklace and such. I totally slutted myself up, going all out. I looked… not good, but it was dark and people couldn’t see too much. 
We went from house to house through two different neighborhoods. We all walked up to the house together and the three of them would say “Trick-or-Treat” and I’d be at the very end and in my deep “manly” voice say, “Trick-or-Treat” and “Thanks!” but it was funny, a lot of the reactions were like, “oh my God, best costume ever” and I got a lot of positive responses, not many negatives. I’m surprised to be honest because my friend lived at the moment in a more seclusive neighborhood and a lot of people here in Arizona are very religious and don’t like or support the LGBT community as a whole. I was already out as gay at that time.
I want to go back a little bit to talk about getting all dressed up. I’d say it took probably 4 hours with putting on the nails, making sure the makeup looked good, doing the hair, putting on the clothes, making sure I felt confident enough, and of course getting down the walk because I had not really worn high heels before that. I wore high heels for the night which was a mistake. I tripped a few times and decided to take them off while we were still out, which was disgusting walking around the neighborhood barefoot. But we circled around the block to go grab my shoes because I was not feeling it, but we still wanted to be out. 
I looked like a hot mess back then. I had oil problems and acne. My friend who did my makeup literally just did like my eyes. I was at my friend’s house and I got all dressed up and I took some pictures in her bedroom cuz she was in the bathroom getting ready and so used her room. You know, I honestly didn’t know what to think about what I saw. I was scared and actually cried. I thought I looked pretty, nothing like supermodel status, but it was scary. I had never even thought about being feminine in any which way at that point. The thought of something different was kind of intriguing. I don’t know if you know this, but I grew up Mormon. My family was really pushing the Mormon beliefs. My grandparents on both sides are Mormon. My dad has now left the church and is now an accomplished tattoo artist, feel free to check him out on social media @JohnHansenTattoo . My mom is still Mormon, so that made me nervous especially later in life when I came out as transgender. When I went home I was still kind of dressed up. I think I changed back into my boy clothing before I went home, but I still had the face on and they asked “how did it go?” and all I said was “it was great, it was great” and I went to my room and didn’t talk to anyone the rest of the night. 
The importance of my first time cross-dressing
The reason why I bring up this story is to show people that I had never even thought about anything like being transgender and that was how it all started. I’m not kidding, within two weeks I was wearing eyeshadow and painting my nails every single day for school every single day. I have some pictures from the following Christmas. I dressed up full glam, well, full glam for back then. For the Christmas party with my family, all the pictures I had full out eye shadow, I loved the eyeshadow. Dressing-up was honestly one of the most important parts of my transition and really helped shape me into the person I am today. If it wasn’t for my friends pushing me to do it, I feel like I would have never felt like I had finally found myself. That’s really the most important part, for you to love who you are. I’m glad for myself that I had realized this, because who knows if it could have been another 10 years before I finally realized this is why I’m not happy with myself. Thanks to those friends freshman year, I realized I did not like looking like a boy, it just didn’t suit me, personality-wise, and everything else. I just thought I looked awful all the time. The second I put on that “dress,” all I knew was that I liked how I looked. 
Thank you for taking the time to learn about my experience with crossdressing for the first time! I definitely think that it’s important for us to communicate with each other, so go ahead and continue to follow my journey on social media and share with me your own stories of discovering a new part of yourself and finding ways to love who you are! 
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