Boyfriend turned into girlfriend crossdresser

So I always take advantage of any opertunity to crossdress. When my girlfriend asked me, do I want to do a makeover? I was like, Hek Yes! She already knows I crossdress. We have been together for awhile and I told her about my little hobby early in our relationship. As soon as I told her she wanted to see me dressed. So I dressed for her and I think she was surprised. There were some critiques about my amateur makeup, and trying to hide my large shoulders. She didn't hate the idea of me dressed. She touched up my makeup and it helped a lot. We sat and talked about it for awhile as she was trying to understand why I did this. It is too difficult to explain to someone. The truth is, I myself don't know why I need to crossdress. I just love seeing myself as women in a tight dresse, heels and stockings. When I see a sexy dressed woman, I want to imitate them. I will try to re-create an outfit I see. I always walk around looking at women's outfits wondering how they would look on me. Anyway I digress, since I have been with my girlfriend have played with me crossdressed several times. On a few early occasions she did my makeup. We had several good sexual nights. Then all of a sudden she was not that interested. She didn't stop me from dressing. Every once in awhile she would go out with her girlfriends and give me the house for a night to crossdress.

Almost a year goes by and on average she gave me one or two nights a month. I was glad to be able to dress but it is lonely. I wanted to play again, do different sexual things but she didn't want to participate. Now out of nowhere she is suggesting we do a makeover. I kind of get it because even for me, my crossdressing can fad in and out for a time but it always comes back.

We picked a night to do the makeover and I was excited. I was a little panicky deciding what to wear. still undecided the night of , I was in the shower trying to make a decision. So strange a straite male in the shower shaving his legs trying to decide what dress and heels he wants to wear. After my usual body shave, I came out of the bathroom smooth and stark naked. There was my girlfriend fully made up in a tight black pencil skirt, red satin blouse, black stockings and tall black heels. Slutty eye makeup and posing In a dominant manner. "Here put these on" pointing to the bed. There was my red satin blouse and black pencil skirt. Black stockings and my black pump heels. Wow nearly matching outfits, I was so turned on.

After I got dressed she ordered me into the bathroom and sit on the toilet. She went to work on my makeup con touring and everything. Almost an hour later with a finishing powder and the glue dry on my lashes. I couldn't wait to see...she was not entirely happy with how it turned out but I thought it was great! Far better then anything I ever did myself. I almost think I could have gone out in public. If she thinks she can do better then I welcome another night.

Anyway I felt super sexy and fem...when I feel that way I want to really feel like a girl...doing girly sexual things like suck dick. After going down on her for a bit, out came the dildo but after the last time she pegged me, I was nervous. It hurt a lot. We started by playing with her double ended dildo. A mixture of licking and dildo penetration I realized I liked how it looked with the dildo sticking out of her pussy. While it was all the way in her, I started to sucking the other end this turned out really well. She was getting pleasure and I felt like a slut sucking cock. After a while of gagging licking and moaning before I knew it she was having an orgasam and squirted. This was a first! My hard on was exploding in my lacy panties. With a quick flip, I was on my back getting deepthroated with a finger in my bio pussy. Then I felt cold lub in my ass and the dildo pushing into me. The initial pain was bad and for a moment I didn't think it would work. She licked the head of my cock and went all the way down my shaft to the base, simultaneously pressing hard on the dildo which poped in my asshole sliding all the way in and the pain was gone. She gently worked it in and out for a few minuets when I exploded a huge load of cum on her face and all over my fake brestes. We laied there out of breath wiping the cum into her mouth. She grabbed my jaw and came in giving me a huge open mouth cum swapping kiss. We swirled our tongues around each other's mouths with the final quantity of cum in my mouth. "Now swallow" she said, so I did. Cum dripping from my chin fully dressed as a women, this was my heaven. When I was younger after cuming I will mediately undress and feel guilty. Now I just stay fully dressed for hours and let the cum dry on my makeup. What a fun night, can't wait to do it again. Maybe next time another CD could join us...