For fun I tried crossdressing, and I found that it was such an unbelievable turn on! I would just paint my finger nails and toenails at first and be that way in my apartment, and that never failed to arouse me. I becme more adventurous and tried putting on make up, eye shadow and lip stick, and it was extremely exciting. Then, I finally got around to trying some female clothing, which I purchased at a used clothing store, and even got some sandals. I really enjoyed the fun and pleasure as well as the excitement of making myself look female - although I have no desire not to be a guy. It is just something which is very interesting and, like I said, exciting. I grew my hair out some, and I have ventured outdoors on a number of occasions and did not receive any secoond glances.
Now, I spend a good deal of time crossdressing in my apartment and on occasion going out. A lot of fun!
I got into crossdressing a few years back. It wasn’t that I wanted to be a girl, just that I found it exciting to pose as a girl. Well, I had a freiend who found out. To my surprise, he thought it was pretty neat and was very accepting of it. In fact, he sound that he found be to be a very attractive girl. For fun we went outtogether like that a few times, and we even kissed. It didn’t long for both of us to begin t enjoy this relationship and become romantically involved. No regrets!
When I was growing up, my uncle Lyle was also my aunt Leslie. Basically he was a crossdresser who lived as a woman. This was known and accepted in my family, and he was always Aunt Leslie. My mom and him got along just fine, and the two of them would go out shopping and for lunch and things like that. To me, it was more or less normal, and I never thought a whole lot about it exactly until I was older.
Then one day I was over at his house, and I ahppened to see him naked in the bathroom. And there he was, with these really nice full breasts and big nipples … and a large penis and balls hanging down between his legs. I was amazed by his dual figure. He just smiled and asked if I thought he looked nice. I said that I thought he did, as I took all of this in. Being quite casual about it, he suggested that I take off my clohtes and be naked, too. I was sort of shy, but it sounded like fun, so I got undressed, and there was Aunt Leslie and me standing there naked together. Well, he started getting an erection, not making any effort to hide it from me, and I watched has penis pushed up big and hard. I strated to get an erection, too. We both smiled and laughed and he felt my erection and I felt his. Then we hugged and held each other, with his large breasts up against me, and we rubbed our erections together. We did this for several minutes, and then he satrted coming. I could feel his liquid pulse out against me. That made me ejaculate and I squirted my cum all over him. We cleaned up and laughed about it. After that time, the two of us began having some very sexy moments together and no one ever knew.
I strated crossdressing when I was fifteen, just for fun and out of being curious. My parents were divorced, so it was just my mom and me. During the summer, when she was at work, I had the house to myself and I was suffering from the usual summer time boredom. One day I saw a bottle of my mom’s nailpolish, a deep red, and I happened to be barefoot, so for the heck of it I painted my toenails. It was daring and fun and I thought that was pretty neat. I just liked walking around the house with painted toenails. Of course, I either had to take it off before my mom got home, or be sure to wear shoes. Anyway, over the next couple of weeks, I began painting my toes all the time and really liking it. I thought it would be fun to go out that way, only I was unsure about doing that as a boy. So it occurred to me … what if I went out looking like a girl? I’m thin and I thought that maybe I could pull that off. I combed my hair around in a more girlish stule, and put on some eye makeup and lip stick. I just wore jeans and flip-flops and a girly looking top. I looked at myself in the mirror and was susprised by what a good looking girl I made.
So I dariningly ventured out. Doing so cautiously at first, but with more confidence when I saw that no one was giving me a second look. I discovered that I really liked seeing what it was like to have a feminine personality, just playing at it, but also finding it a genuine turn on, too. I spent most of that summer being a girl, and I even talked to some boys - and had to practice getting the voice down, which I did fairly well.
That was how I got started, and I secretly continued doing it to this day, years later. I liked being both Jim and Jessie, and I know that I would genuinely miss my other female persona now if she wasn’t available for me to enjoy. It’s funny, because I never thought of myself as being a crossdresser, and I am certainly not gay. Yet. this is the way it is and I have no regrets!
We always have a framer’s market and craft fair in the park, and lots of times I’ll walk through it. Well, I met this blonde girl who worked at a booth selling craft items, and I thought that she was different and quite appealing. Anyway, over the next few weekends, I made sure that I stopped by to talk to her. She was friendly and nice and seemed to enjoy talking to me. Then I asked her if she would like to gewt something cold to driink when she took a break, and she that would be fine. So there she was in her cut-offs and sandals and looking quite attractive. Like I said, I had just immediately found her extremely appealing. I suggested that maybe we could go out for a bite to eat some time in the evening. Well, she seemed suddenly reluctant. I asked her if she had a boyfriend, and she said, no. So I persisted, and managed to talk her into going out the next night.
We just went to a casual place and got dinner. We had a good time sitting and talking, and I found out that she was my age and originally from Nebraska. She wasn’t exactly what you would call beautiful, but she had very nice and interesting features. After dinner, we went walking along looking at the shops and still talking. Finally, Jamie, said that there was something I should know about her. I thought - oh, don’t tell me she’s married or a lesbian or something. I was completely surprised when Jamie confessed that she was actually “Jimmy,” and a boy. I couldn’t believe it. I didn’t know what that meant, exactly. So I dumbly asked if that meant he wanted to be a girl and get an operation and all of that, and she/he said, no. That he just liked dressing up and more or less pretending to be a girl, and saying that he was not gay - which was my next question. Of course I was confused, and I admitted it. I also said that I still found her to be very attractive. Well, Jimmy said that was sweet and was flattered. And I confessed how I wished that he/she really was a girl. She said how outwardly she was and sort of teased me about that, and I said how I liked that part and wasn’t really bothered about her being a him, mostly because I couldn’t see her as being a him. The evening ended on a friendly note and I went home still wondering how I felt about all of this.
That next weekend, I went back to see Jamie in the park, and she was quite happy that I had, afraid that now I would avoid her. I said, no way. Well, we were both happy, and she suggested that we could go out for something to eat again that evening, which was fine with me. So we went, and things were quite friendly between us. We even held hands and laughed about it. We had a good time and talked some more, and I confessed that I still liked being with her. Jamie didn’t mind that, and asked if I wanted to go over to her place. So we did that, and I was a little nervous, not knowing what to expect exactly, and she was a little nervous, too. We had some coffee and sat together on the sofa and talked. We were both wearing sandals, which we took off. While we were sitting there, we looked at one another, and it was kind of like neither of us knew what to do. Very slowly we leaned over and we kissed. It was quite romantic, so we did several more small kisses. She remarked that this was not something she was used to doing (with another guy), and I pointed out that it was quite nice, and she agreed. So we began to kiss more passionately, using our tongues. We held each other and we began touching and caressing.
Jamie laughed and said how she didn’t have much in the way of breasts, but revealed that she had been working on that a little bit, using some narural herbal and hormone creams. We both laughed, and I pulled her top up and off and then she got rid of her bra. Jamie did have small sort of flat breasts, and her nipples were sizeable. I playfully and kissed and sucked on her nipples, which she found stimulating. She got me to take off my shirt and she kissed and sucked on my nipples. While she was doing that, I felt her hand slide down to feel the erection that I had. Encouraged, I went ahead and slipped her shorts down and there was her penis, also erect. This was proof that she was definietly a boy. Yet, I found that exciting. I began to play with her penis, and she began opening my pants and playing with my erection. We kissed some more, and in the next few minutes we had our clothes off and were enjoyably naked. It was quite thrilling for both of us.
Jamie suggested that we go into the bedroom, so we did. We climbed on the bed and stretched out together, kissing and hugging and fondling and caressing. We rubbed our penises together, and then she took mine into her mouth to suck on. So a moment later, I did the same to hers. This was the first time that I had ever been with another guy, but I was surprised by what a turn on this was. After about an hour, we masturbated one another to a tremendous ejaculation that felt wonderful. We were both very taken by the experience and the next day when we got together, neither of us had any regrets or seconds thoughts. That evening we got back together at her house and we got naked in her bedroom again, making out like crazy. Finally, Jamie suggested that we fuck. We didn’t have any condoms, so we just used some lubrication, and I put my hard penis in and I fucked her. It was so incredibly satisfying to let myself come fully in her. I think that right then we both knew how good our relationship was.
That was two years ago, and Jamie and I now live together and we have throughly enjoyed and taken great delight in every minutes of our being together. Everyone just sees us as a normal in love couple, and could ask for more?
I have a friend who is a crossdresser. I was surprised when he confessed that he liked to do this, and thought that he was pulling my leg. So he showed me. I was amazed to see him as a girl. His hair was short, but he combed it into a kind pf page boy, which looked great. He didn’t overdo the makeup, but put on just enough. And he didn’t get done up in dresses or high heels or anything that extreme. He just wore jeans with a kind of girly top, painted his fingernails and toenails. He was veyr sucessful, I think, because he didn’t try to be overdone, but just look like a regular girl. It was quite a transformation, and I would have never guessed that she was actually Tim.
Well, I actually thought that it was pretty neat, and I could sort of understand why he thought it was fun to try gender switching. His name was Tim, but when he dressed up, he called himself Tina, his female persona. Anyway, I was really impressed that he was so successful, and he said that sometimes he had started being daring enough to go out in public that way, and how nobody even looked twice at him. For fun, we decided to go out together, with him dressed as Tina. It was summer, and we went wandering around, and there was a farmers market and craft fair in the park. While we were looking at things, there was my mother, out shopping. She saw us, and there was nothing we could do, and we were stuck. So we just braved it out. I introduced Tina and my mother really thought nothing of it. Of course Tim and I thought that was an absolute blast.
Anyway, when I was back home, my mom commented on Tina, saying how nice she was and everything, and asked if I was starting to date Tina. I felt kind of bad about decieving her, so I confessed the whole thing. I said that Tina was Tim, who she knew. Mom was completely surprised and amazed, pretty much just like how I had been. My mom and dad are divorced, and I know that my dad would have been appalled. But mom was very open minded about it. She said that Tina was very attractive, and asked if I was going to start dating Tim. I was embarrassed, and I told her that I wasn’t gay. Mom was very nonchalant about it, though. She said that she didn’t see that as being gay, and how maybe Tim and I just felt like being close as friends. I didn’t know quite what to think about that. The next day I told Tim about the whole thing. He was kind of embarrassed because my mom knew his secret, but in a way he thought that was pretty neat that he didn’t have to hide it from her, either. His own mom knew that he crossdressed sometimes, and was not entirely approving of it. Anyway, he said that it might be fun if we were sort of dating and acted like a couple. It was an interesting idea and I wasn’t exactly opposed to it. I mean, Tina was awfully good looking, and I really found it easy to think of Tim as Tina and a girl.
So, we started going out that way, and nobody thought anyting at all about it. Tim started coming over to my house as Tina, and my mother was perfectly accepting of it, even our starting to be a little affectionate with one another. It didn’t feel like I was being gay, although in a way I did find it exciting to be with Tim as another boy like that. So that was over a year ago, and Tim/Tina and I have been happily dating the whole time. It’s kind of like having the best of both worlds.
I had the same experience with my mom. Just for fun she painted my toenails, which I thought was kind of cool. Then she teased me into trying some makeup and got me looking like a girl. I was amazed by the transformation, and I really liked it. It was like discovering a whole side to myself that I had no idea even existed or that could be that much fun. I started being a girl at home sometimes when I felt like it, and got quite comfortable with it. Then, my mom and I went out to lunch, with me as a girl. Nobody even looked twice. It was really something to get to experience this. I would say go for it and give it a try. I think that you will be surprised by the results and that you will like the experience very much.
I don’t know if this quite a crossdressing story. But one evening my mother was sitting on the sofa and we were watching Tv, and she decided to piant her toenails. I happened to be barefoot, and when she was finished, she asked if I wanted my toenails painted. I said sure, just foe the heck of it, so she painted them a kind of dark plumb. Well, it was different seeing my toenails painted like that. Anyway, we went to bed, and the next morning I of still had painted toenails, Mom thought that it was cute, and she teased me and said that I should try some makeup. So I let her put makeup on me, and started looking like a girl. Mom thought that I looked nice, and said that maybe I should try dressing like a girl sometimes, if just around the house just for fun.
So far I haven’t gone that fra, although since my mom thinks that I should, I’m feeling tempted. Have any other boys had this experience with their mothers?
A friend and I decided, just for fun, to see how it would be to crossdress. We painted our fingernails and toenails, and carefully put on some makeup. We didn’t have any girly clothes, so we just wore top and cut-offs and flip-flops. We were both surprised by what good girls we actually made. Feeling confident, we went out dressed like that and completely got away with it!
I can tell you, it was quite exciting for both of us, and we have continued to enjoy this activity!