Crossdressing Success Stories are real-life stories from everyday crossdressers like you and me. They allow us to share in our successes, no matter how small. As we share our experiences we grow in our own transgendered walk, and shine a light that inspires others.
Please take a moment to share your story. Include your femme name, a brief introduction and then a 500-750 word success story. If you’d like, please share a photo of yourself as well. I’ll share your crossdressing success story with readers of Crossdresser Heaven in a few weeks.
If you’re still considering whether to share your crossdressing story, take a moment to browse through crossdressing success stories submitted by readers of Crossdresser Heaven.
Bless you for blessing others,
Vanessa
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My ” name ” is jasmine but my birth name is jacob. I am a homosexual crossdresser and my story starts when I was 4 and my older sister dressed me up in a dress. I liked it back then too but whenever my father came home he would make me take them of. As I grew older I now see I was more of a girl than a boy. When me and my friends played power rangers I would want to be the pink one or would want to play house instead ( I was the mother ). I would hang around with the girls and I now realize that I did and still do have a mostly love but slightly hate relationship with drama. About a year ago when I was eleven my sister was having a slumber party downstairs and I decided to hang out down there to annoy my sister. Her friends were talking about cute boys at school while doing their nails. I sat on the couch and pretended to watch tv but I was really wanting to sit and talk and be like one of the girls. I shoved the thought out of my head because my family was VERY religious., but still I started to examine my sisters friends. I stared with unknown jealousy at their hair and earrings and makeup and voice and painted toenails and frilly pink girl clothes and one of the friends saw me staring. I immediately started watching tv again but the friend called me over. My parents were out that night and I was somewhat worried about what they were going to do to me without adult supervision. I went over and they huddled and started to whisper. A few startled gasps and angry looks later I was sitting down next to them just wandering what was going to happen. The girl asked while painting her toenails orange ” is there anybody you have a crush on at school?” and I told her no and she asked who all the girls liked this year so I started to tell her about the boy who was also in football ( I didn’t want to be in it but my father made me ) and how the girls would kill to feel his soft blond hair or see his perfect 6 pack and found myself staring dreamily off into space thinking about the boy with the girls all staring at me. My sister then handed me a bottle of hot pink nail polish and said ” tell us about the other boys ” so I awkwardly healed the bottle wondering what to do with it while I told of other boys. My sister interrupted me and said to start on my nails or she would take the bottle away from me. I stared in shock at what she just said and resumed talking about the boys while opening the bottle of polish. By the end of the hour we had all painted our nails and were comparing them while talking about which male actors were the cutest. I discovered what I was doing but didnt stop. The girls huddled and talked again while I examined my perfect hot pink nails and toenails. The then grabbed my by the arm and ran me ustairs, giggleing. Now that I think about it I was giggleing too. The took me upstairs where they’re bags were and gave me some clothes. I immediately went to the bathroom to put the bra and panties on. I came out feeling weird but somehow happy. One of my sisters friends who was in theater arts pulled out a beautiful brown wig with long wavy curls and also handed me one of her dresses it was a light pink and I put it on with the brown wig while the other girls did my makeup. In the end I didn’t recognize the girl in the mirror. I had mascara with purplish eyeliner and pink lipstick and blush. The gave me the final touches: earrings, jewelry, and shoes. The earrings stung but In the end I looked amazing. I had the perfect amount of makeup and the shoes were black heels that opened at the toe so you could see my nails. I had a simple necklace and the earrings were tiny silver hoops. I swirled in delight and hugged every one of them they giggled and handed me more outfits to try on. I was so happy! I could actually passs for a not pretty or cute but beautiful girl! The frend who let me use the wig also let me keep it as a reminder of the night. I kept the makeup on and changed into some of my sisters pajamas. I let the girls tie up my hair in a ponytail and they fought me how to apply makeup and choose outfits and everything! We went downstairs and watched the twilight movies almost drooling whenever Taylor lautner takes his shirt off. As I fell asleep next to my sister and my best girl friends I heard my sister say ” good night jasmine, my baby sister.” it’s been about a year since then and I still crosdress at home. Everytime my sister has a slumber party she makes sure to invite our girlfriends ( not actually girlfriends but in the way of close friends) and make sure our parents are out so I can turn back into jasmine. I’m getting better at the transformation: I can style my hair in any way I want to and I can apply my own makeup perfectly and choose the outfits and jewelry I want to with my sister. I can also make my voice sound like a girls so it males me feel better about it. I have one secret but steady boyfriend and he knows that I crossdress. Other than him he is the only one at my school that knows and when were around people we act like close friends but whenever there isn’t people we secretly kiss or hug or we sometimes even make out. The farthest we have gone was us both ” tripping” in the showers onto each others….. You know what I mean 🙂 my boyfriend is soooo nice and cute and we sit next to each other in ever class so he can pass me notes and i can pass them back feelimg like the day is just beginning! I am very much like a boy in the fact that I play football and do boyish things like get dirty but to be honest I have no taste for that kind of stuff. I am very emotional like a girl but mask it very well. ( p.s my boyfriend is the boy I was talking about to my sisters friends about when they were doing their nails! Thank god he’s gay! I had been subtly flirting with him and he finnally flirted back! He has a locker next to mine so I usually get an “accidental” bumping into after he gets out of the shower 🙂 it takes all my strength to not smile or laugh or you know what all over the locker room floor and to act mad or annoyed with him when he bumps into me is unbearable biut he knows I mean to do it again whenever the chance is available ) all my sisters friends know I’m gay but my parents still don’t. The only out of the house experience I had crossdressing was whenever me, my sister, her boyfriend, my boyfriend, and all my sisters friends with their boyfriends went to go see the midnight showing of a romance movie. I had told my parents I was going to bed and transformed into jasmine and snuck out the window and went to the front porch as jasmine. I used my best girl voice to successfully fool my parents into thinking I was one of my sisters friends ready for the movie- slumber party and he let me in. My sister and her friends played along and my father dropped us off at the movie theater at midnight. I saw my boyfriend and ran into his arms. He hugged and kissed because I hadn’t seen him for a week and this was our first real date. I saw my pink lipstick all over his face and he was smiling like crazy! My sister came up and quietly asked me if he knew. I said yes and she told him that if he ever hurt her little sister she would personally beat the crap out of him. We bought popcorn and a drink for the both of us and met up with our group. All the girls were with their dates talking and cutting up when we were finnally allowed to go in. It was such a great movie! At one point when me and my boyfriend both reached for the popcorn he healed onto my hand and we stayed like this until one of the main characters family members dies and I start sobbing along with the other girls because it is so sad! My boyfriend puts an arm around me and pulls me closer to console me, I am so exited by this I kiss him softly on the lips and he kisses back even though I have mascara all over my face and am still sniffling :).after the movie when we are walking out he takes me by my denim jacket and kisses me with more passion than I though possible. He then says ” tonight was amazing. How bout the same thing next weekend?” I love my boyfriend! I smile and turn to ask my sister if she will have another slee
pover next week and I see shes already standing behind me smiling like she was the happyest person on the world. She act like she is thinking about it then says “YES”! She then walks up to her boyfriend and grabs his face and kisses so hard he is pushed up against the wall! I giggle and turn to my boyfriend who turns his head quckly away from where he was just staring. He was staring at where my penis is and wonder if my skirt is see through. I smile and kiss him, aware of both the bulge in his jeans amd the bulge in my skirt touching. It was a long story but I wish any otter gay crossdressers good luck and hope they are successful in their more feminine life’s like I am!
~ Jasmine <3
Its jasmine here again to tell you about what happened recently! I came out! I told my parents and showed them and my dad was shocked and kind of angry but my mom was extremilly exited! The bad news is that things are going to get kind of inaptopriote from this point on so if you don’t want to hear it leave now. So the other day a couple of hours before I came out me and my boyfriend were the only ones left in the locker room. The coaches had left already and so did all the other students. I was In the shower when someone cameup from behind me and hugged me. I smiled and turned around. It was my boyfriend! I stared at his you know what and grabbed it. He smiled ad I could feel his and mine beginning to get stiff. We both touched ours together and started to kiss. I let my tounge go into his mouth and felt his go into mine. I kissed him harder but he pulled away. I asked him what was wrong and he felt like he was cheating on jasmine. I understood but was still ready for him to come closer. He didnt. I got mad and dried of and put my boy clothes on. When I got home my parents were sitting at the table with my sister next to them. I asked what was going on and the said that I was a crossdresser. I agreed and they stared. They said they wanted to see me like jasmine and I went into my sisters room to get the suitcase where I keep jasmines things. I chose a pink shirt and skirt with hoop earrings and orange nail polish. I got my pair of red toms on and applied mascara and lipstick. I put on my wig and let it fall over my shoulders. The bra and panties felt more comfortable than usual and I was ready to take on the world. I went back to the table as jasmine and said in her voice “….. So what do you think?” my dad stared and said that when I was home I could dress up as a girl whenever I wanted to. I was super happy by this and also told them I was gay. They had actually suspected it and accepted it. I squealed and hugged my big sister. I called my boyfriend over and we saw each other. I stood with my arms crossed in the doorway. He ran unto me and twirled me around. I giggled and embraced him like I hadn’t seen him in 10 years. I introduced him to my parents and my mom said she wanted to talk to me in private. I went up to her room where she handed me a purse and makeup bag and said that I have “good taste”I smiled and went back downstairs. My boyfriend and dad were watching a baseball game together and I sat down next to my boyfriend with my feet tucked in and my head on his shoulder. He caressed my face and brushed the hair out of it and kissed me on the cheek. My dad stared sadly and continued watching the game. The next day at school I came out to some close girl friends of mine and asked them if they wanted to go to one of me and my sisters slumber party’s. 2 out of five said they could. I gave them my adress and told them to get ready to get fabulous on Saturday. They came over with my sisters friends and we all started the night ny playing apples to apples. After that we put on mud masks and did our nails in our pjs. We all talked about who liked who and what was going on in the dating eorld and whose actresses boobs were fake. We all started giggling and I announced the challenge that the first person the fall asleep would get their bra frozen. We then went into the living room where all the sleeping bags were and watched the secret life of the American teen for two hours then one of my friends fell asleep and her bra ended up in the freezer. She woke up and we had a fashion show because my friends wanted to see me in othe girl clothes and my sisters friends wanted to see how jasmine has grown up. I go upstairs to my room which was going to have to be redone ( it had dark-blue walls with posters of people on dirtbikes 🙁 ) and find my orange dress and heels with yellow purse and gold earrings. They match my nails and I apply my eye makeup. I grab my yellow purse and red necklace and go downstairs. They all gasp when they see me. I did too when I saw myself in the mirror. I was beautiful!! The girls examined me and commented on my exelent hair. My BFF Abbie said that I was prettyer than a real girl. I blushed and said thank you and got changed back into my tanktop and pajama pants upstairs. I washed to makeup off and brought my bag downstairs. I applied everyones makeup and they all said I should get paid for my skill. I blushed again and re-fixed my hair into the ponytail I had had it in before. That next day when it was just me and my boyfriend at my house we went into the garage which had the van with the mattress in the back once we got back there he pulled off my skirt and panties and pulled me closer towards him. I unbuttoned his shirt and pants and took them both off and he took my shirt off of me. We lay there. Me naked him also naked spooning me with joy. I smiled and turned towards him. Our cocks touched and I could tell both of ours had been stiff for a while. We humped each other for a while and then I lay on top of him with my faceon his rapidly moving chest. He kisses me on the head and brushes the hair out of my face. For the last time until I’m older I feel his cock with mine and we both start humping again with me secretly hoping it will happen again before I die. Again it was long ( that’s what HE said 🙂 ) and it was innapropriote but I wanted to update you on my gay crossdressing life
Fabulously yours ~ jasmine