Mark was my first cross-dressing/ transgender exploration. He identified himself as a bisexual cross-dressing transgender individual. Neatly put, he enjoyed wearing women's clothes and got off on it regardless if he was with a man or with a woman. Okay, maybe that was a little too neat and blanketed, but I covered most of the corners. Most of the time he'd been with men, he was in a dress. And most of the time he'd been with women, he had been undressed. It was all about attraction for him. And it was all new to me.
I didn't know much cross-dressing and Mark was more than willing to share the sexual side of that world with me. He was attracted to me and wanted to me open and honest from jump. So he would show me his she little by little to see my level of comfort of who he was and who she could be. At first, it was just him in a dress and the two of fooling around and making each other wet. He would put on a dress and become her and she would eat me out. And when she was done, she insisted I return the favor and suck h on her clit, which was her dick and we would go back and forth reciprocating pleasure until we were both moist between the legs. I had to adapt to getting use to calling his dick a clit whenever he was her. It was challenging. For the most, it was because I never had a clit in my mouth before. And I definitely never had a 5 inch clit in my mouth that had balls and semen. The only clit I was familiar with was my own and what strong masculine hands could done it in a clockwise motion. That clit experience, I could retell in my sleep. But it was a learning process. Occasionally we would fuck and he would fuck me as him and not her, which was familiar for me. After all, I've never been fucked with a clit either.
But interchanging him and her and her and him was enough for Mark to show me. He wanted to be fully her and he wanted to fuck me as her. One night, I agreed. Curious and intrigued, I agreed to let him fuck me as her -- all dressed up.
I remember that evening quite clearly -- a few years back. We had gotten a room together as he wanted to make it as private as possible. We had picked up dinner and some ingredients for mixing beverages. We talked idly while got prepared and I asked as many questions as I could think of as he transformed into her. And in between his make-up and tights, he plowed me with drinks. Several of them. I think he was more nervous about fully revealing her to me that me being revealed to all of her. Normally, the nervous person does the drinking. Not the person who makes you nervous. And as I patiently waited and swigged for another pour drink, Mark became her. I forget her name, it's like Contessa, Theresa, Vanessa, -- something with a lot of Ss and As. And whoever she was, she was not pulling any stops. She had on a black corset, barely laced in the back -- I helped finished the lacing when she paraded in front me. She had on thigh-high faux leather boots, fishnet tights and a miniskirt that questioned the imagination. All black, all form fitting. All for me. And as she stood in front of me in all her glory, she dangled a pair of fuzzy handcuffs that she intentionally brought for me.
Extending her my arms out to give her my wrist, I let her handcuff and guide my hands to the most appropriate place on the bed while she had her way. Securing my hands above my head around a bed post, she climbed on top of me so that she parted her legs inches from my face, bringing to my attention she was not wearing any panties. As she raised her skirt, she told to lick her clit (cock). So I did. She said lick again. And I did. I continue to lick on command until she told me to suck her clit. I took all five inches of clit into my mouth as she rode my faced and rocked her hips. Then, she reversed directions so that her clit would still be in my mouth, but now she could lean down and have my clit in her mouth. We were like this for several long moments, both of us moaning, both of lightly wetting the bed from arousal. She then lifted herself off of me to grab one of the many dildo and toys she had brought for such occasions. She came with a long flesh like fist and told me to spread my legs. That thing was huge. Larger than any real cock I ever fucked and by the looks of that thing, I was not going to be able to get that in my tight pussy no matter how wet I was. But she was determined now the less. And spread my legs she did. She started slowly, getting the tip of the top fist in my pussy, making firm but gentle thrust in me. With one hand she reach above me and unfastened my handcuffs so that I had something to hold onto while she fist toy fucked me. He thrust the object became more demanding and forceful as she ordered me to spread my legs further wanting me to take it deeper. Deeper, I tried. It was huge and it was being rammed into me over and over again. When she would break with the toy, her hand replace it jutting inward with the same motion and ferocity. And then the toy was back again. I moaned and groaned at pleasure and disbelief, all in one. I was being fucked by the biggest -- thing -- ever and it still could make it's way completely in my pussy. But little did I know that while she was fucking, I had inched my way toward the edge of the bed, as if body was trying the escape the sexual tyranny of such a toy. But she did not stop fucking with the fleshy fist for one bit. She fucked and I'd move away. And she fuck so more and I'd moved further away. Until ... I was fucked off the bed. I had literally fucked until I capsized. I had flipped off the bed, pussy wet and abused and face down in utter shocked that I had been fucked so hard my a toy. By a woman with a toy. By a man dressed as a woman with a toy.
The night wore just the same until I blacked out and woke up next to him, not her. He clothes has been strewn across the floor along with mine. The bed sheets had been twisted around the both of us. Light was beginning to pour from the new day. As I looked over the mess we had made, I couldn't believe all that we had done. All that I had allowed to be done. It was the closest I had ever gotten to having sex with a woman. I looked down at him while he slept and before getting up and showering, I laid back down once again replaying the events of the night that I could remember. If anyone had a chance to peek in watch us in engage in the wild sex we had, they would've easily identified two women going all out. What could I have said other than, "I'm with her."