Read the prologue if you want to understand the characters further, but if you just want to get into it then
I was starting to have my first doubts about what I had signed myself up for. Here I was, standing in the hallway in a miniskirt, a low-cut top and a short black wig with my cock sellotaped down waiting for a guy to knock on my door. A guy who I had invited round to take my virginity even though I had never met him before.
About 6 months after I started cross dressing 2 years ago I decided to put myself to the test. I was bored of being David; I wanted to be Emily, the name I had given my alter-ego. I went on chatrooms and displayed myself over webcams, seeing how many people I could trick into thinking I was a girl. They all fell for it. I should bloody hope so as well with the amount of time I spent practising my act. However, I soon began to get restless. I watched porn and played with myself but I needed to be satisfied by a man. I wouldn’t rest until I had one deep inside me telling me how beautiful I was. I posted pictures of myself online and guys commented on how stunning I was, as well as a couple of lesbians: they were shocked when I told them I was still a virgin. It felt good to finally be coveted by men, to be the object of their desire, to be able to drive them crazy. I imagined them wanking over my pictures. But it still wasn’t enough.
There was this one guy, Benj, who was really interested in me. He was bi-sexual and so he didn’t even care when I told him I was really a guy. He said I was still the most beautiful thing he’d ever seen. I would spend hours talking to him online, he was funny, smart and quite cute. He was 22 and had bright ginger, curly hair with freckles to match, but not in a geeky way. He was still fairly big and was well-toned. I would run home from school, get changed and talk to him over the internet. This went on for a few weeks, and then he asked the big question.
“Whereabouts do you live?” He asked over the webcam chat.
“South of England, Wiltshire” Was my reply. I didn’t anticipate him living anywhere near me.
“Really! I live in Hampshire about an hour’s drive away.” He then started to persuade me that we should meet up, he reminded me how I was always going on about how much I wanted to lose my virginity. I started thinking and decided that he was the only other person who knew about my secret life and I might as well lose myself to someone I could trust. I gave him my address and told him a time when the house would be empty. My sister was at college in America and my dad was at work as usual.
I was looking forward to it and started counting down the days. When it finally came I couldn’t wait to get changed and become Emily, the name I had given my alter ego. I didn’t put on any underwear beneath my skirt as I knew that I would want to begin the sex as soon as Benj came through the door. However, as the time creeped closer I began to get nervous. What if he was some thief or a sex trafficker and I was letting him into my house? What if he thought I was terrible in bed?
I didn’t have time to think anymore as the clock was stopped by three knocks. I tiptoed towards the door and looked out of the peep-hole. It was definitely him. I stood still for a few seconds longer and then gave up my resistance and pulled the door open. Benj looked me up and down from head to toe.
“You don’t like it?” I knew everything had gone wrong already.
“No, the opposite. You look even more gorgeous in person and I just didn’t think that was possible.” I tried to work out if he was just being kind. I guessed he wasn’t as he stepped through the door and kissed me on the lips. Just softly. I closed the door and let him kiss me again. This time it went on for longer and I felt his tongue slide in between my lips. I received it with my own. I rested back on the wall and Benj leant over me, our arms clenched around each other. Then he picked me up and carried me upstairs, still making out on the way. I nodded to a door through which was my Dad’s room. I chose it because of the double bed.
Benj lowered me down gently and sat down next to me. I asked how we were going to do this and he just told me to trust him. He lay me down flat and rolled me onto my side, explaining that in this position my rectal muscles would be more relaxed. I lay there facing the wall while listening to what Benj was doing behind me. I heard him squeeze some liquid out of a bottle and him rubbing his hands together. Then I felt his finger trace along my anus, spreading a gel with it. I assumed it was lube. Then he pushed one of his fingers into my ass still rubbing the lube around. Even though he was barely an inch in it felt really good and I let out a small moan.
Benj laughed, “If you think that’s good you’ve got a big shock left to come yet.” I heard his trousers come down and I felt him rolling onto the bed behind me. He pulled his body up next to mine and lifted one of my legs in the air. “You ready for this?” He asked while pulling the hair of my wig out of my face. I grunted as a reply, too nervous to speak. The head of his cock prodded my make believe pussy, already rock hard.
The second it was in I screamed. I had fingered myself before but now my ass was being pulled apart from within. I was able to restart my breathing process as Benj pulled it out only to stop again as he rammed it back in. Each time he repeated this it went further in. Time went agonisingly slowly as he did it again and again. I had never experienced such an amalgam of pain and pleasure. A small trickle of blood snaked down my leg accompanied with biting pain but Benj continued. Then I felt his pubic hair brushing against my back. Now he started to build up a rhythm of thrusts pulling all the way out and slamming it back in again. Now that the grimacing pain was subsiding the feeling of sheer pleasure was building. I was being filled with a man who coveted me for my beauty. My groans started to get higher pitched and louder. This just seemed to encourage Benj who started to speed up, unconsciously my hips joined in with his rhythm, moving backwards as he pushed forwards. Then I felt an explosion somewhere inside me. I only realised it was Benj’s ejaculation when he gripped his arms tight around me and sighed. He must have made contact with my prostate gland as I let out an animalistic roar. It must’ve been extremely loud as I didn’t hear my dad entering the house, or detect him climbing the stairs, or notice him standing in the doorway of the bedroom seeing his son being treated like a common slut.
The fight didn’t last long. My Dad’s explosion ended with Benj being thrown out of the house and him staring at me in my sister’s clothes, still shaky from the sex. My Dad was a bloke’s bloke, he watched the footie, went down the pub and played darts. He was an imposing figure at 6”5, bald, slightly overweight and with tattoos all down his arms. My Dad didn’t even know I was gay, let alone that I was fantasising about being a girl. He shouted and ranted as I sat on his bed looking at the floor. He told me how ashamed he was and how he’d always been disappointed in me: apparently he’d always preferred my brother Ethan because he was someone who he could be proud of.
I ignored most of it until he told me that I could never do this again and that he was going to make sure of it. Now it was my turn to fight back. I told him just how important this was to me, and, just as he was about to say something else I made an off-hand remark about my mum.
“You are my son and you will do as I say” He reminded me.
“Maybe if you’d been less controlling then maybe Mum wouldn’t have left.” There was a void silence so overwhelming that meant I had no choice but to continue. “Yeah that’s right, you just try and manipulate everyone around you. It’s sick. I can see why she left now, and- and, you know what. She made a lucky escape.” It wasn’t fair and I knew it. My Dad was still sore from my mother’s abandonment, but I couldn’t apologise under these circumstances. To do so would be to give in, and my current state of mind wouldn’t let me do that. We both stood face to face. My Dad walked out the door.
I sat on the sofa waiting for him to come home. I didn’t bother getting changed, it didn’t matter anymore. I eventually drifted asleep but I remember looking at the clock at around 3 in the morning and noting he hadn’t returned. As I slept I dreamed of Benj and my experience earlier, at least that memory was something to hang on to.