April 1, 2014

I am single and in my early twenties, and live alone. I was sort of curious about what it would be like to crossrss, so bought some makeup and nail polish andsome girl’s clothes at a thrft store. Well, I tred it around my plae, and practicedgetting everything down so I looked pretty good. It was a kind of teasing turn on to see myself as a girl. Finally, I got brave and ventured out dressed that way. It ws so exciting and gave me such an unbelievable erection! I could see people just thinking that I wasa girl, and it was so amusing because they had no idea that I had this enormously stiff penis under it all. Needless to say, I had to masturbate when I got home, and it was so great rubbing my hard penis to a climax while in my girl mode. After that, beause it was such a fantastic turn on, Ihave started to go out regularly, and I always enjoy coming home and masturbating the hardest erection that I have evr had, to the most intense ejaculation that I have eer expereinced! Something about mysecret he-she persna never fails to thrill me in way tha I would have never imagined a year ago!

March 13, 2014
Me, too

I ust read a stor from Dec, aout the boy who found that he liked crossdressing. My story is about the same. M parets were divorc and it was jst my mom and me. Durin the summer shewas atwork, and of course I was feeling bored. One day, just for fun, I tried some of her makeup. I put on some eye shadow and liptick, and combedmy hair ina girlsh sort of style the best I could. I was surprised to have this rather cute girl looking back at me in the mirror! Well, it was kind of a thrill doing that, so I started getting into i around the house while my mother was at work. I panted my fingers a few times, but of course I always had to take the paint off before my mom got back. I found that I could get by with painting my toenails and that Ididn’t have to worry about my mom seeing that.

  Well, I got adventurous and one day I decided to go out dressed like that. I just put on jeans, nd wore flip-flops, with my toenails painted, put on some makeup, and a girly sort of top. I hd a blast wanderng around all day being a girl! Like Dec, Dan became Dani, and I had a whole new identity that I realy enjoyed having! Soon, I was doing this regularly, and having hebest time. A few boys my own age - whome I didn’t know - even talked to me, thinking that I was a girl. Although I’m no gay, I thought that was pretty neat and I liked it.

That was a few years ago, and my mother never found out, of course. Nor did anyone else. Now I have my own place, and I freely enjoy being Dan and Dani. I often go to a super market wher they don’t know me as a guy, and  go as ani and always am thrilled to be sen as a very successful girl.

March 12, 2014
Why Not?

I knw that most of these stories about guys dressing as girls, but I thought I would throw mine in about a girl wh gets by as a guy. I’m quite feminine, only that I’m completely flat chested, have short hair, and can pass as a boy.  I have often put on a pair of cut-offs and have sunbthed topless on te deck. I also go without a top on aroud the house all the time, even infront of my father and brother.My mom says, why not? I still feel sexy showing off my nipples. Mom, whose breasts are quite full, feels too self-conscious of course to go around the house without her top on. So I guess that there are some benefits to being fla chested!

March 9, 2014
Mom, too

  I read a couple of stories on here about boys who have moms that encouraged them to crossdress. For my mom painted my toenails one day, which I thought was pretty cool. I’m slender and blond ad fair skinned. She remarked on how I would probably make a passible girl. So,  she heped me with some makeup and adding some touches, and I really did make a good looking girl. I found the transformation not only interesting, but I liked having the chance to see ort of what it ws like to be a girl. I tried crossdressing around our house for a while, and started t become quite comfrtable with it, and my mom thought it was nice. For laughs, she got me some girlish clothing and sandals, and we wnt out together that way - mom and daughter, and it was a blast! So now, about half the time, I get to be her daughter Dani, and the rest of th time her son, Danny. I like having the dual identity.

February 8, 2014

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!

December 29, 2013

 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!

December 25, 2013

 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.

December 25, 2013

 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!

December 25, 2013

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?

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