Her First Halloween Ch. 01

It was Halloween night and I had an exciting night planned for me. My best friend, Andrew, and I were going to dress up in costumes, go to a club downtown, and get our party on. Now it wasn't going to be just the two of us, though, as his girlfriend, Karla, was coming along as well.

For costume ideas I was at a loss. I had no idea what to wear and decided to put on one of my football jerseys and jeans to just go as a football player. Yeah, it wasn't the most creative idea, but I thought it would do fine. I was sorely mistaken.

I arrive at Andrew's house. Karla and him are already in costume and they look great. Andrew is dressed in native american garb and so is Karla as she is dressed as "Pocahontas", if you even want to call it that. The costume looked stunning on her. She was wearing a short brown dress that hugged her tight and went barely a quarter of the way down her thigh. The dress had Native American tassels hanging from it and she, along with Andrew, had war paint on their face.

Andrew is about 6 feet tall and nearly 200 pounds with a lot of muscle. Karla is a smokeshow. She's about 5'2'' and while I wouldn't say she had a petite build, she was on the smaller side, and had an unbelievable ass. As for myself, I'm relatively small in stature. I was maybe 4 inches taller than Karla and weighed about the same, but where she had curves, I was just skinny. I might as well have been a girl standing next to Andrew. I've always had a hard time putting on weight and whenever I'm around other guys I can't help but feel awkward with how tiny I am comparatively.

I greet them and we make our way to the kitchen. We get to talking and drinking and I get a pretty good buzz going. We're about a 45 minute uber ride to the city and we still had some time left before we had to go. Karla out of the blue asks me, "So David are you really going to go to a club dressed like that?!"

I was caught off guard and didn't really know how to respond. I had no other costumes and I told her as much. She said, "No, no, no, that just won't do. Come with me."

She takes me and leads me to their bedroom. I say their bedroom but it's really Andrew's. We're all in our early 20s and he still lives with his parents, but Karla is there all the time.

She sits me on the bed and starts digging through the closet. She laughs to herself and says, "Wait a second I think I found the perfect costume here." She pulls out a bag and takes the costume out. It was some sort of small white material and I was soon able to piece together the costume. It was a pink and white strapless mini dress that finished with a frilly skirt that flared out at the bottom. It was embroidered with glitter and other shimmery material. I gasped out loud as she then grabbed a pair of angel wings out of the closet. It was obvious she wanted me to dress as some sort of slutty angel. I didn't know what to say, but ended up coming out with, "I'm sorry Karla, but you can't be serious."

"I'm soooo serious," Karla says as she places the wings on the bed. "Believe me you'll look great and it's halloween! Guys dress like girls all the time today. This is what I wore last year! I'm just upset I lost the halo that went with it."

I was at a loss for words, but this was a secret desire of mine. I've always wanted to cross dress but I was always too shy and ashamed to go forward with it. I've gone through life thinking I was 100% straight, but women's clothes just made me feel different. I had even tried on some of my mother's things in the past but only when I was younger. Guilt made me stop but I still think about doing it. Even with that being said, I did not want to go out in public dressed like this, especially in a costume this revealing.

"I don't know Karla, I don't think I'd be able to pull it off," I say in hopes that she will back off and pick out a new costume for me to wear. I didn't want to sound too eager to try on this costume, when deep down I really wanted to.

"Nonsense," Karla says, "Just leave it to me I'll make you look super convincing!"

I hesitated staring at the dress. I didn't want to admit to my best friends girlfriend how excited I was thinking about putting on the costume. She noticed my apprehension and grabbed my hands and looked me in the eyes.

"Pleaseeee. Just try it on for me. Let's see if I can make you look good." I was getting extremely worked up as she rubbed my arms. Being a virgin, any sort of female touch turned me on immensely.

I finally cave in and say, "Fine, I guess there's no harm in trying".

"Yay!" she shrieks as she leads me into the bathroom. "If you want me to make you look good we can't go half ass." She hands me a few bottles. "So cover your body in this and wait a few minutes before hopping into the shower. Then use these bottles on your hair and body before finishing up."

The first bottle I used got rid of most my body hair. "Wow, she was taking this seriously," I thought. As I was running in the shampoo, I hear Karla open the bathroom door. She then proceeds to walk into the shower with me, completely nude. I desperately try to cover up.

"Jesus, Karla, what the hell are you doing!" She just laughs.

"Stop it, David and don't even bother covering up. I've seen plenty of dick in my day, and I need to help you remove the rest of your body hair. Plus, I'm in here showing you all my goodies. The least you can do is show me yours." I reluctantly move my hands away from my privates. She smirks and says, "Wow, your bigger than I thought you were down there, but it's still so small compared to Andrew's." She starts rubbing the cream on my legs and works her razor. She eventually gets to my private parts. As she finishes shaving that area, she starts rubbing me up and down. I start getting hard almost immediately.

"Oh yeah you like being all smooth just like the little girl you are, don't you," she says as she is fondling my balls and penis. "I can see it in your eyes, you can't wait to dress up." I feel the urge to cum but she pulls away and turns the shower knob to start blasting freezing cold water. I go soft and she goes, "We can't have you blowing your load just yet."

I get out of the shower smelling like roses and walk into the bedroom. I see the costume laid out for me on the bed. I can't keep my eyes off it. The entire experience in the shower plus the alcohol had my mind in a blender. I hated to admit it but she was absolutely right. I couldn't wait to dress up and the way she talked to me had me so worked up, I was shocked I didn't explode right then and there. And what was all that about Andrew's "size". Was he really that much bigger than me? I shudder at the thought. I look over to my left and see Karla, who's now fully clothed in her costume, with a smirk on her face. How long was I just staring at the costume? The fact she had redone her makeup after the shower said quite a while.

"Like what you see? We're almost done here, let's get some makeup on you." She sits me at the vanity table and starts applying all sorts of makeup on me. As we're doing this, she's feeding me shot after shot of liquor. I go from tipsy to real drunk, real fast.

I couldn't tell you what makeup she used, as I've never forayed into that area, but by the end of it I couldn't believe I was looking at the same person in the mirror. What stuck out the most were my now beautiful and full pink lips, but my entire face was done up. She finished it off with a blonde wig. I legitimately looked like a girl.

I was once again at a loss for words but I didn't have time to talk as she stands me up. and says, "Here now let's put the dress on!" She places it over my head and body and stands back for a second before saying, "No wait that won't work." She takes the dress off me and goes back to the closet. She grabs another bag and takes out silicone breasts. I question why she even owns something like this but before I can say a word she's putting some sort of adhesive to my chest and sticking the breasts on. She then goes to the hamper in the room and takes out a white bra.

"Here we go, much better," she says smiling. Maybe it was all the alcohol in my system but before I could argue she snaps the bra into place. Then she places the dress over my head and leads me to a mirror.

"Here take a look."

I look in the mirror and I can't believe my eyes. To say I looked passable was an understatement. The tight dress hugged my breast and body until it got down to around my hips as it loosened out a bit toward the skirt portion, which finished with a white fluffy material at the bottom. The dress was unbelievably short though. I'm lucky Karla decided to wear a slightly longer dress last year than she did this year because on me this angel costume barely covered my privates. Any sort of sudden movement and my ass would have been on full display. In fact, you could easily see the bottom of my cheeks when I wasn't even moving around. I went to grab the boxers I came here with for modesty and she shot that down immediately.

"No way David there's no way I'm going to let you ruin that beautiful costume with those horrible underpants. Hold on I'll think of something." She looked around the room and even back in the hamper, but no luck. She sighed defeated. I thought she would hand me back my boxers. Instead she reaches under her dress and pulls down the panties she's wearing. She hands them to me and I stare in disbelief. In her hands is a small, frilly, pink thong! The one she had been wearing all day! I was practically sweating.

"Come on don't be a weirdo, David. Just grab the thong and put it on. Don't worry I'm clean and I can get away with no panties for tonight with how tight my dress is. A stray wind or anything like that will have that skirt of yours flying all over the place, leaving your bits completely on display!"

I grab the thong and slip it up my legs and under my short dress. The feeling of the material on my penis was unreal. The panties were moist in the crotch area and I discovered I really loved the feeling of the panties splitting my cheeks.

She hands me some small pink heels that matched my dress. I put them on and found it weird how they fit me just about perfectly. There's no way we were the same size, but before I could question it Karla starts dragging me out of the room. "Come on, we've gotta get a move one before we miss the uber. It's been here for 5 minutes already."

I freeze forgetting all about Andrew. My best friend of years. He'll have no respect for me if he sees me like this, even with it being a Halloween costume. "Oh wait, Karla, I completely forgot about Andrew! I don't want him to see me like this. How am I going to explain this to him?"

"Oh come on, don't be such a wuss! Besides Andrew is so drunk right now he doesn't know what's going on. Before I hopped in the shower with you, I told Andrew you weren't feeling well and went home. He mumbled something to me and passed out on the couch. I think he's still asleep, so it may just be me and you tonight."

My nerves calm as I walk out of the room with Karla. As we're approaching the front door I'm a wreck. The click clacking of the heels were not only difficult to walk in, but made this situation seem much realer. Sure, I loved the way the dress felt but I couldn't even think about going out in public like this. I attempt to shout out that there was no way I could do this. But before I could, I felt a strong hand squeeze my ass. I squeal in surprise and turn around to see Andrew.

"Where you going, cutie?" He says as he grabs my hand and leads me and Karla back to his bedroom.