To recap, our protagonist didn't want to dress up for a halloween party, so his girlfriends decided it was time he joined in the fun. They styled his hair, did his makeup and put him into an 'Alice' dress. However, the disguise worked a little too well, as Chris Smith has taken 'Tilly' back to his house after a passionate kiss on the street corner...
Chris put his key in the door and unlocked it. It swung open into a dark hallway with wooden floors, and he said "Ladies first," indicating for me to go inside. I was so nervous, if he found out I would be done for. My stilettos tapped on the wood floor, and I bent down to unbuckle and remove them. Chris squeezed my ass under my dress, dangerously close to my 'parts' lay beneath my white tights.
"Come on," he said, and took my hand to lead me up the stairs, and into his bedroom. It was very masculine, there were posters of famous footballers and sexy women on the walls, and I noticed he had a huge pile of weights in the corner. No wonder he's so fit, I found myself thinking. I sat on the bed, unable to say anything because I was so nervous. I really wanted to kiss him, but I couldn't let him find out who I was.
He sat next to me and brushed my hair out of my face again, seemingly his trademark move. He put his arms around my waist and pulled me in tight for a kiss. We were passionately making out again, not just me and a man but me and Chris Smith! I found myself wondering what if Leila found out, and realising that I didn't really care. He started to slide down the puffed sleeve on one of my shoulders and I had to stop it.
"Chris," I said, trying my hardest to sound feminine, "I can't do that, I hardly know you." My voice was trembling.
"Man!" He exclaimed, "Worth a try, right? I guess we'll have to get to know each other better then." My heart jumped, I don't know how but he made me feel so special then.
I apologised to him and we kissed again, before he turned out the lights. I lay in his bed, keeping my dress on so he didn't find out, and he lay behind me. After a few silent moments, he slid his left arm underneath my neck and hugged me with his right arm. Maybe it was just the alcohol, but it felt amazing.
Sunlight woke us in the early morning, streaming through the window. I didn't know whether I should get up or wait for Chris to leave for work. He as still hugging me, and I also felt him poking me in the back. His penis was right next to my hole, and it turned me on so much. He had clearly woken up, because he held the top of my tights and started to pull them down. I grabbed his hand and stopped him, sliding down under the covers. He was still wearing his boxers, which I pulled down to reveal his hard penis, the first I had ever seen. It was pulsating, he could hardly control it. I opened my mouth and started to suck his cock, moving my head back and forth. He started making out of breath noises, and pulling my head further into his cock. I felt completely like his bitch; I loved it. I ran my hand up and down his cock as I was sucking until he exploded with sperm into my mouth. I swallowed it all, and though it didn't taste great, loved feeling like such a whore. But I was still a bit drunk, and had been lucky not to have been caught out yet, so this would be the end of it. I could always remember my night as a beautiful girl.
"I'd better get off," I told Chris, as I stood up. I hoped I could get out before Leila was up.
"No need to hurry, I have to get to work in about half an hour, I can give you and Leila a lift if you like."
A huge weight dropped in my stomach, "A lift?"
"Yeah to school, Karen said you two were friends. She'll by now, go get ready with her and I'll call you guys when I'm done."
That was it. I would have to explain all this to Leila. Unless Karen had planned it and Leila knew. My fate had been sealed, and I slowly walked out of Chris' room, and down the hall when Leila popped out of a door, and pulled me into her room.
"What the hell are you doing!?" She half whispered to me. "That's my brother!"
I looked at her beautiful face, mortified, and incredibly embarrassed that I was sat there in such an iconic girly dress. "We didn't do anything.." I stammered.
"Damn right because my brother isn't a sissy-fucker!" She took a deep breath, "Right, you can't come to school like that, you'll have to borrow a uniform off me. If I were you though as soon as he drops us off I'd fuck off home and change unless you want everyone to know you're a sissy."
I nodded slowly, and unzipped the dress and took it off, along with my tights, leaving me stood there in just my bra and panties. She smiled, she was loving this. On her bed there was quite a big shirt and some boot cut black trousers. Clearly girls, but not that bad. I went for them and Leila stopped me, "No, that's my uniform. Yours in on that chair" She pointed to a chair in the corner of the room with a small pile of clothes on it. I sighed, but knew I couldn't complain, so I pulled the sheer black tights up my legs, pulled up the short black pleated skirt next and zipped it up. It reached a few inches above my knee. Finally I buttoned up the tiny, tight, white blouse that my 'breasts' were nearly spilling out of.
"You can't go looking like such a slut," Leila said as she finished her makeup. She sat me down and put my hair into a ponytail, before removing last nights makeup and applying some lighter foundation, mascara, blusher and little bit of eyeliner on the bottom of my eye.
"I'm ready to go!" Chris shouted up.
I think I can safely say I'd never felt so nervous in my whole life. "Come on," Leila said, taking me by the arm and leading me out of her room. "Oh, almost forgot, here," She passed me a pair of simple black pumps with a bow on the front to put on. I stepped into them and allowed her to drag my schoolgirl self out of her room and down to Chris. I was so embarrassed, again. I caught a glimpse of my reflection in the mirror, and I looked undeniably like a teenage schoolgirl. One of the gorgeous, really popular ones. As a breeze from the door my skirt whip around my thighs I realised, I was not out of the woods yet.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/in-wonderland-pt-2.aspx">In Wonderland, Pt. 2</a>