Kissing Crossdressers

Kissing Crossdressers
Fabulous Tgirl Alice share 5 of her most favorite outfits/style with us. Some words by ...
▶ Name: Tabea ▶ Location: Zurich, Switzerland ▶ How long you have been crossdressing : Since 25 ...
What causes people to crossdress? It’s a fascinating subject with many answers. In most societies, ...
▶ Name: Cheryl ▶ Location: Ireland ▶ How long you have been crossdressing : My crossdressing experience ...
When I was in high school I was a bit socially awkward and especially around girls. I’d been with a number of girls, sure, but many of them left a lot to be desired. One year, a new family moved into my parent’s building and my life changed. That was because within that family, there was a very effeminate young male that I found on the back porch in total drag.
I was just coming upstairs from track practice when I noticed him. I was immediately struck by how beautiful he was in girls clothes and makeup. He was Puerto Rican descent and had full sensual lips that were even more enticing by the matte cranberry red lipstick.

I was frozen when I saw him. When he saw me, he looked horrified and backed into a corner thinking that I was going to wail on him. I assured him that he was safe and contrary to his fears, I actually thought he was really cute. The words just came out of nowhere because I was so smitten.
We wound up sitting on the back porch steps talking well into the night. And it was obvious that we had a mutual attraction for one another. We decided to slip into the basement stairwell of a vacant apartment in the building so that we could talk more freely which led to hand holding, which then led to the moment where I leaned in to kiss him. That led to another kiss, then another, then another, then more prolonged kissing and caressing. The next thing I knew, he was sitting on my lap while we continued kissing.

Knowing that our families would wonder where we were, we reluctantly decided to part and head back to our apartments. But this felt too good to abandon so we would meet regularly at the basement stairwell where we would kiss for hours. The level of intimacy was unmatchable and no girl in the neighborhood could even come close to what I experienced with this cross dresser. Every night I would rush from the dinner table just to meet up so that we could share those sensual kisses.
Unfortunately, I went away to college and when I returned that fall, I was told that this family had moved to California after the father of the family found a job there. This was before email and social media, so we never got a chance to reconnect.

I did find some consolation in the fact that one of our neighbors talked about how the son in the family cried the whole time he was leaving. I could have been wrong, but I was hoping that those tears were because we would not be together again.
Sorry if this story does not end in this cross dresser and I fully making love, but our kissing sessions were filled with the most sensuality that I’d ever experienced and something that will always hold a special place in my heart.
No “happy ending,” but a beautiful memory nonetheless.
No “happy ending,” sadly. But it’s a beautiful memory.
What a beautiful story and sad 😢, I had the same sort of thing happen to myself when I lived in Exmouth Australia and John went back to the United States. I have kicked myself ever since for not being truthful to my feelings.
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Fabulous Tgirl Alice share 5 of her most favorite outfits/style with us. Some words by ...
▶ Name: Tabea ▶ Location: Zurich, Switzerland ▶ How long you have been crossdressing : Since 25 ...
What causes people to crossdress? It’s a fascinating subject with many answers. In most societies, ...
▶ Name: Cheryl ▶ Location: Ireland ▶ How long you have been crossdressing : My crossdressing experience ...
When I was in high school I was a bit socially awkward and especially around girls. I’d been with a number of girls, sure, but many of them left a lot to be desired. One year, a new family moved into my parent’s building and my life changed. That was because within that family, there was a very effeminate young male that I found on the back porch in total drag.
I was just coming upstairs from track practice when I noticed him. I was immediately struck by how beautiful he was in girls clothes and makeup. He was Puerto Rican descent and had full sensual lips that were even more enticing by the matte cranberry red lipstick.

I was frozen when I saw him. When he saw me, he looked horrified and backed into a corner thinking that I was going to wail on him. I assured him that he was safe and contrary to his fears, I actually thought he was really cute. The words just came out of nowhere because I was so smitten.
We wound up sitting on the back porch steps talking well into the night. And it was obvious that we had a mutual attraction for one another. We decided to slip into the basement stairwell of a vacant apartment in the building so that we could talk more freely which led to hand holding, which then led to the moment where I leaned in to kiss him. That led to another kiss, then another, then another, then more prolonged kissing and caressing. The next thing I knew, he was sitting on my lap while we continued kissing.

Knowing that our families would wonder where we were, we reluctantly decided to part and head back to our apartments. But this felt too good to abandon so we would meet regularly at the basement stairwell where we would kiss for hours. The level of intimacy was unmatchable and no girl in the neighborhood could even come close to what I experienced with this cross dresser. Every night I would rush from the dinner table just to meet up so that we could share those sensual kisses.
Unfortunately, I went away to college and when I returned that fall, I was told that this family had moved to California after the father of the family found a job there. This was before email and social media, so we never got a chance to reconnect.

I did find some consolation in the fact that one of our neighbors talked about how the son in the family cried the whole time he was leaving. I could have been wrong, but I was hoping that those tears were because we would not be together again.
Sorry if this story does not end in this cross dresser and I fully making love, but our kissing sessions were filled with the most sensuality that I’d ever experienced and something that will always hold a special place in my heart.
No “happy ending,” but a beautiful memory nonetheless.
No “happy ending,” sadly. But it’s a beautiful memory.
What a beautiful story and sad 😢, I had the same sort of thing happen to myself when I lived in Exmouth Australia and John went back to the United States. I have kicked myself ever since for not being truthful to my feelings.
Your email address will not be published. Required fields are marked *
Save my name, email, and website in this browser for the next time I comment.

Fabulous Tgirl Alice share 5 of her most favorite outfits/style with us. Some words by ...
▶ Name: Tabea ▶ Location: Zurich, Switzerland ▶ How long you have been crossdressing : Since 25 ...
What causes people to crossdress? It’s a fascinating subject with many answers. In most societies, ...
▶ Name: Cheryl ▶ Location: Ireland ▶ How long you have been crossdressing : My crossdressing experience ...

Friend Gets Attracted to his Crossdresser Friend

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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