1st time crossdressing and how it all began.
It all started back in 2008 when I was only 20 years old. I dated a girl name Melynda, whom I've been dating for awhile back then. We basically did everything together like shopping, hanging out and so on. One day I slept over her house and forgot my pj's. She said "That's okay, here you can borrow mine." At the time I really didn't think about it but I really like the way they felt on my body. Soft, smooth and of course comfortable. I told her that I really like the way they look and feel and she said to me "you can go ahead an keep them." So I was like okay, yay! As time went by I told her about how I really like her pj's and that the way they feel on my body. She looked at me with a smile on her face and told me that I should try on her other clothing. Me being her boyfriend I was like okay, sure why not? So we went back to her place and I tried on some more of her clothing. Then she said to me "You wanna try on some lingerie and fuck me?" So I did and and it felt amazing! Dresses in soft silky smooth lingerie and fucking my girlfriend.
As days pass dresses in her clothing while fucking her she says to me "hey, you wanna try on some makeup?" And I was like yeah, why not? As she did my makeup I was scared at 1st, eyeliner was really close to my eye. An after she was finished she was like "wow!" "You look beautiful all made up and dresses in my clothing." An then all of a sudden she surprised me an said "you wanna have strap-on sex.?" I was like do I really wanna go through an do this? And get plowed by her? Eventually after some talking I agreed and we bought a dildo with a harness. I was scared at 1st but when I was relaxed and all lubed up she slowly slid it up inside of me. An thats when I realized it felt ready good and I love anal sex! After awhile she kept on dressing me up and fucking me with bigger and bigger dildos. It felt amazing, an now I was her sissy boy toy anal slut.
After awhile we broke up, for other reason just like all couples. Now that I was alone I had no one to dress up for and have fun with. So I decide to not let that let me down. I went out on my own and bought makeup, women's clothing and lingerie. I also bought my own dildo to play with. A few years later we ran into each other and I told her what I've been doing and up to. She was like, I'm proud of you and knew you were bi. Then she said to me "I'm having a party this weekend and let me introduce you to my friend." In all honestly I really didn't know what to say so I just said yes. Eventually the weekend came and I went to the party. And there at the party she introduced me to her friend who was another CD named Chloe. I asked her out and then we eventually started dating.
It turned out to be one of the best relationship I've ever had. It was fun because we both dressed up together and did each others makeup. The best part about it, is that Chloe was the top or so I thought. And from there, that's when I became a real sissy boy toy anal slut. Even though I'm non-pass I still love the feeling of dressing up and putting on makeup. Other then that, I would always dress up for her in the bedroom and while having sex I started to realized that I love dick.! Real dick that is. Of course playing with my dildo is always fun but having real dick is better. Even though it was a great relationship we ended up breaking up, we had our problems just like all couples do. In the end we were both bottoms and it didn't end up working out for the both of us.
Later on as the months pass maybe years an then I met my boyfriend. He would always have me dresses up and stayed dressed up. I would walk around his place in sexy clothing during the day and sleep in lingerie at night. Of course after awhile of dating him, he took our sexuality to new levels. Besides the great sex, after fucking he would stick a dildo in my butt and have me keep it inside of me. The only time he'd let me take it out was when were about to fuck. An after awhile he bought me a chastity lock and would keep my sissy boy dick locked up. I love it when he would say to me "I'm keeping you locked up while I fuck your boypussy and make you cum." Eventually after fucking for awhile he was able to make me cum without touching myself. It felt good when he would use my dildo on me and make me cum too. It got to the point where I was able to cum without touching myself and have him make me cum.
During our sex there were times when he would just cum in my boypussy. An other times where he'd cum in my mouth and have me sick him dry. I would never waste a drop of his cum if he came in my mouth. An yes, I swallow. He'd also loved to see me cum all over myself when ever I came. In all honestly it was the best sex when he came in my boypussy and have me put on panties to keep it inside of me. The best part about all this is that I was always in women's clothing or sexy lingerie while we were having sex. There were times when he would pound my ass for hours and stick dildos inside of me to keep me lose. An let me tell you, I'de love keeping those dildos warm inside me and sleeping with them inside of me at night long. Eventually like all relationships it didn't work out in the end and we ended up breaking up.
To this day I still dress up and play with my dildo. Like almost every night and if not then every other night. Playing with my dildo is fun but real dick is even better. I do miss getting my tiny butt pounded. My boyfriend at that time told me that he loved pounding me and my tiny butt. He said to me that it was because he likes seeing his big dick going inside of me an my tiny ass. Regardless of the fact I didn't really care because I just love dick. It feels amazing inside of me and I truly do love the feeling. I also like chubby older men. But other than that, I love dick, I love cum and can't get enough of it. That's why I love dildos and keeping them inside of me while dressed up as a CD.
P.S: I love other crossdressers, transgender m2f and older chubby men.
As days pass dresses in her clothing while fucking her she says to me "hey, you wanna try on some makeup?" And I was like yeah, why not? As she did my makeup I was scared at 1st, eyeliner was really close to my eye. An after she was finished she was like "wow!" "You look beautiful all made up and dresses in my clothing." An then all of a sudden she surprised me an said "you wanna have strap-on sex.?" I was like do I really wanna go through an do this? And get plowed by her? Eventually after some talking I agreed and we bought a dildo with a harness. I was scared at 1st but when I was relaxed and all lubed up she slowly slid it up inside of me. An thats when I realized it felt ready good and I love anal sex! After awhile she kept on dressing me up and fucking me with bigger and bigger dildos. It felt amazing, an now I was her sissy boy toy anal slut.
After awhile we broke up, for other reason just like all couples. Now that I was alone I had no one to dress up for and have fun with. So I decide to not let that let me down. I went out on my own and bought makeup, women's clothing and lingerie. I also bought my own dildo to play with. A few years later we ran into each other and I told her what I've been doing and up to. She was like, I'm proud of you and knew you were bi. Then she said to me "I'm having a party this weekend and let me introduce you to my friend." In all honestly I really didn't know what to say so I just said yes. Eventually the weekend came and I went to the party. And there at the party she introduced me to her friend who was another CD named Chloe. I asked her out and then we eventually started dating.
It turned out to be one of the best relationship I've ever had. It was fun because we both dressed up together and did each others makeup. The best part about it, is that Chloe was the top or so I thought. And from there, that's when I became a real sissy boy toy anal slut. Even though I'm non-pass I still love the feeling of dressing up and putting on makeup. Other then that, I would always dress up for her in the bedroom and while having sex I started to realized that I love dick.! Real dick that is. Of course playing with my dildo is always fun but having real dick is better. Even though it was a great relationship we ended up breaking up, we had our problems just like all couples do. In the end we were both bottoms and it didn't end up working out for the both of us.
Later on as the months pass maybe years an then I met my boyfriend. He would always have me dresses up and stayed dressed up. I would walk around his place in sexy clothing during the day and sleep in lingerie at night. Of course after awhile of dating him, he took our sexuality to new levels. Besides the great sex, after fucking he would stick a dildo in my butt and have me keep it inside of me. The only time he'd let me take it out was when were about to fuck. An after awhile he bought me a chastity lock and would keep my sissy boy dick locked up. I love it when he would say to me "I'm keeping you locked up while I fuck your boypussy and make you cum." Eventually after fucking for awhile he was able to make me cum without touching myself. It felt good when he would use my dildo on me and make me cum too. It got to the point where I was able to cum without touching myself and have him make me cum.
During our sex there were times when he would just cum in my boypussy. An other times where he'd cum in my mouth and have me sick him dry. I would never waste a drop of his cum if he came in my mouth. An yes, I swallow. He'd also loved to see me cum all over myself when ever I came. In all honestly it was the best sex when he came in my boypussy and have me put on panties to keep it inside of me. The best part about all this is that I was always in women's clothing or sexy lingerie while we were having sex. There were times when he would pound my ass for hours and stick dildos inside of me to keep me lose. An let me tell you, I'de love keeping those dildos warm inside me and sleeping with them inside of me at night long. Eventually like all relationships it didn't work out in the end and we ended up breaking up.
To this day I still dress up and play with my dildo. Like almost every night and if not then every other night. Playing with my dildo is fun but real dick is even better. I do miss getting my tiny butt pounded. My boyfriend at that time told me that he loved pounding me and my tiny butt. He said to me that it was because he likes seeing his big dick going inside of me an my tiny ass. Regardless of the fact I didn't really care because I just love dick. It feels amazing inside of me and I truly do love the feeling. I also like chubby older men. But other than that, I love dick, I love cum and can't get enough of it. That's why I love dildos and keeping them inside of me while dressed up as a CD.
P.S: I love other crossdressers, transgender m2f and older chubby men.
7年前
